Phenylalanine derivatives as herbicides

ABSTRACT

Phenylalanine derivatives of the formula I  
                 
where the radicals are as defined in the description, and the use of these compounds as herbicides and/or for regulating plant growth is described.

The present invention relates to phenylalanine derivatives of the formula

in which

-   -   R¹, R², R⁴, R⁵, R¹³ and R¹⁵ independently of one another are         hydrogen, halogen, hydroxyl, mercapto, nitro, cyano,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,         C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio,         C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl,         C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl,         C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl,         C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,         C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy,         C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl,         C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl,         C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl,         C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,         C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy,         C₃-C₆-alkynylthio-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶;     -   R³ is hydrogen, halogen, mercapto, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-alkenyloxy-C₁-C₄-alkyl,         C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,         C₃-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₆-alkynylthio-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl or CO—R¹⁶;     -   R⁶ is hydrogen, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₁-C₆-alkyl;     -   R⁷ is hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl or         C₂-C₆-haloalkynyl;     -   R⁸ is methyl, ethyl, C₁-C₆-alkoxy or hydroxyl;     -   R⁹ is hydrogen or C₁-C₆-alkyl;     -   R¹⁰ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl or         C₁-C₆-haloalkoxylcarbonyl;     -   R¹¹ is halogen, mercapto, nitro, cyano, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,         C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy,         C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl,         C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₂-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl,         C₁-C₆-alkylthio-C₁-C₄-alkyl, C₂-C₆-alkenylthio-C₁-C₄-alkyl,         C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,         C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy,         C₃-C₆-alkynylthio-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶;     -   R¹² and R¹⁴ independently of one another are hydrogen, halogen,         hydroxyl, mercapto, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,         C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio,         C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₃-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy,         C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio,         C₂-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl,         C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl,         C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl,         C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,         C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy,         C₃-C₆-alkynylthio-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶; and     -   R¹⁶ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,         C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,         C₃-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylamino or         di(C₁-C₆-alkyl)amino; or     -   R⁷ together with R¹⁰ forms a C₃-C₄-alkylene or -alkenylene         chain, where the C₃-C₄-alkylene or -alkenylene chain may carry         1-3 substituents from the group consisting of halogen, nitro or         cyano and/or one carbon atom of the C₃-C₄-alkylene chain may be         replaced by a heteroatom selected from the group consisting of         oxygen, sulfur and nitrogen and/or by a carbonyl group,     -   and the agriculturally useful salts of the compounds I.

Moreover, the invention relates to

-   -   the use of the compounds I as herbicides,     -   herbicidal compositions which comprise the compounds I as active         substances,     -   processes for preparing the compounds I and for preparing         herbicidal compositions using the compounds I, and also     -   methods for controlling undesirable vegetation using the         compounds I and/or     -   for controlling the growth of plants,     -   compositions for regulating the growth of plants, which         compositions comprise the compounds I as active substances,     -   processes for preparing compositions for regulating the growth         of plants using the compounds I, and also     -   methods for regulating the growth of plants using the compounds         I.

Numerous amino acid derivatives are disclosed in the literature; WO 01/21584, for example, describes tyrosine derivatives which can be used for treating chronic inflammatory conditions.

EP-A 805 147 discloses amino acid derivatives which can be used as calcium channel modulators.

WO 97/19908 describes phenylalanine derivatives whose phenyl ring is preferably substituted by fluorine and which can be used as fungicides.

JP-A 02088549 teaches derivatives of amino acids which are preferably derived from proline, serine or threonine. The compounds described have antithrombotic action.

WO 97/05865 discloses amino acid derivatives which are preferably SO₂-substituted at the amino group group and are used as C-proteinase inhibitors.

DE-A 33 326 333 discloses carboxylic acid derivatives suitable for preparing medicaments.

JP 3294-253-A teaches amino acid derivatives as inhibitors of cholecystokinin and gastrin receptors.

It is an object of the present invention to provide herbicidally active compounds.

The object also extends to the provision of compounds suitable for regulating the growth of plants.

We have found that this object is achieved by providing the phenylalanine derivatives of the formula I defined at the outset.

Furthermore, it has been found that the compounds I are also suitable for regulating the growth of plants. In this respect, we have found compositions for regulating the growth of plants, processes for preparing these compositions and methods for regulating the growth of plants using the compounds I.

Owing to the asymmetrically substituted α-carbon, these compounds are present either as racemates, enantiomer mixtures or as pure enantiomers and may, if they carry chiral substituents on the α-carbon or have further centers of chirality, also be present as diastereomer mixtures. Furthermore, depending on the substitution pattern, the compounds I can also be present as diastereomer mixtures. Preference is given to compounds of the formula I in which the α-carbon has the S configuration. Hereinbelow, these compounds are also referred to as S enantiomers.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action of the compounds I. Thus, suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four C₁-C₄-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionat and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic moieties mentioned in the definition of the substituents R¹ to R¹⁵ are—like the term halogen—collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl moieties, can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen denotes in each case fluorine, chlorine, bromine or iodine.

Examples of meanings are:

-   -   halogen is fluorine, chlorine or bromine;     -   C₁-C₄-alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,         1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;     -   C₁-C₆-alkyl is a C₁-C₄-alkyl radical as mentioned above or, for         example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,         2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl,         1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,         3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,         1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,         2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,         2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,         1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl;     -   C₃-C₄-alkenyl is a mono- or diethylenically unsaturated radical         having 3 or 4 carbon atoms, such as prop-1-en-1-yl, allyl,         1-methylethenyl, but-1-en-1-yl, but-1-en-2-yl, but-1-en-3-yl,         but-2-en-1-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl,         1-methylprop-2-en-1-yl or 2-methylprop-2-en-1-yl;     -   C₅-C₆-alkenyl is a C₃-C₄-alkenyl radical as mentioned above or         is a mono- or polyethylenically unsaturated radical having 5 or         6 carbon atoms, such as, for example, n-penten-1-yl,         n-penten-2-yl, n-penten-3-yl, n-penten-4-yl,         1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,         3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl,         2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,         1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,         3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,         1,2-dimethyl-prop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,         1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl,         n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl,         n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl,         3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,         1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,         3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,         1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,         3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,         1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,         3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,         1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,         1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,         1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,         1,3-dimethyl-but-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,         2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,         2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,         3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,         1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,         1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl,         2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,         1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,         1-ethyl-2-methylprop-1-en-1-yl or         1-ethyl-2-methylprop-2-en-1-yl;     -   C₂-C₆-alkenyl is a C₃-C₆-alenylkyl radical as mentioned above or         ethenyl;     -   C₂-C₄-alkenyl is a C₃-C₄-alenylkyl radical as mentioned above or         ethenyl;     -   C₂-C₄-alkynyl is: ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl,         n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl or         n-but-2-yn-1-yl;     -   C₃-C₆-alkynyl is a C₂-C₄-alkynyl radical as mentioned above or         n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl,         n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl,         n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,         n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl,         n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl,         n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl,         n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl,         3-methylpent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl,         3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl,         4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl;     -   C₂-C₆-alkynyl is a C₃-C₆-alkynylkyl radical as mentioned above         or ethynyl;     -   C₃-C₆-alkenyloxy is a C₃-C₆-alkenyl radical as mentioned above         which is attached to the skeleton via an oxygen atom (—O—);     -   C₁-C₄-alkoxy is a C₁-C₄-alkyl radical as mentioned above which         is attached to the skeleton via an oxygen atom (—O—);     -   C₁-C₆-alkoxy is a C₁-C₆-alkyl radical as mentioned above which         is attached to the skeleton via an oxygen atom (—O—);     -   C₃-C₆-alkenyloxy is a C₃-C₆-alkenyl radical as mentioned above         which is attached to the skeleton via an oxygen atom (—O—);     -   C₃-C₆-alkynyloxy is a C₃-C₆-alkynyl radical as mentioned above         which is attached to the skeleton via an oxygen atom (—O—);     -   C₁-C₆-alkylthio is a C₁-C₆-alkyl radical as mentioned above         which is attached to the skeleton via a sulfur atom (—S—);     -   C₃-C₆-alkenylthio is a C₃-C₆-alkenyl radical as mentioned above         which is attached to the skeleton via a sulfur atom (—S—);     -   C₃-C₆-alkynylthio is a C₃-C₆-alkynyl radical as mentioned above         which is attached to the skeleton via a sulfur atom (—S—);     -   C₁-C₆-alkylsulfinyl is a C₁-C₆-alkyl radical as mentioned above         which is attached to the skeleton via a sulfinyl group (—SO—);     -   C₃-C₆-alkenylsulfinyl is a C₃-C₆-alkenyl radical as mentioned         above which is attached to the skeleton via a sulfinyl group         (—SO—);     -   C₃-C₆-alkynylsulfinyl is a C₃-C₆-alkynyl radical as mentioned         above which is attached to the skeleton via a sulfinyl group         (—SO—);     -   C₁-C₆-alkylsulfonyl is a C₁-C₆-alkyl radical as mentioned above         which is attached to the skeleton via a sulfonyl group (—SO₂—);     -   C₃-C₆-alkenylsulfonyl is a C₃-C₆-alkenyl radical as mentioned         above which is attached to the skeleton via a sulfonyl group         (—SO₂—);     -   C₃-C₆-alkynylsulfonyl is a C₃-C₆-alkynyl radical as mentioned         above which is attached to the skeleton via a sulfonyl group         (—SO₂—);     -   C₁-C₄-haloalkyl is a C₁-C₄-alkyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, chloromethyl,         dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,         trifluoromethyl, chlorfluoromethyl, dichlorofluoromethyl,         chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl,         2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,         2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl,         in particular chloromethyl, fluoromethyl, difluoromethyl,         trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or         2,2,2-trifluoroethyl;     -   C₁-C₆-haloalkyl is a C₁-C₆-alkyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e. for example, one of the radicals         mentioned under C₁-C₄-haloalkyl or 5-fluoro-1-pentyl,         5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl,         5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl,         6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl,         6,6,6-trichloro-1-hexyl or dodecafluorohexyl;     -   C₂-C₆-haloalkenyl is a C₂-C₆-alkenyl radical as mentioned above         in which some or all of the hydrogen atoms may be replaced by         halogen atoms as mentioned above, in particular by fluorine,         chlorine and bromine;     -   C₂-C₆-haloalkynyl is a C₂-C₆-alkynyl radical as mentioned above         in which some or all of the hydrogen atoms may be replaced by         halogen atoms as mentioned above, in particular by fluorine,         chlorine and bromine;     -   C₁-C₆-haloalkoxy is a C₁-C₆-haloalkyl radical as mentioned above         which is attached to the skeleton via an oxygen atom (—O—);     -   C₃-C₆-haloalkenyloxy is a C₃-C₆-alkenyloxy radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine;     -   C₃-C₆-haloalkynyloxy is a C₃-C₆-alkynyloxy radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine;     -   C₁-C₆-haloalkylthio is a C₁-C₆-haloalkyl radical as mentioned         above which is attached to the skeleton via a sulfur atom (—S—);     -   C₃-C₆-haloalkenylthio is a C₃-C₆-haloalkenyl radical as         mentioned above which is attached to the skeleton via a sulfur         atom (—S—);     -   C₃-C₆-haloalkynylthio is a C₃-C₆-haloalkynyl radical as         mentioned above is attached to the skeleton via a sulfur atom         (—S—);     -   C₁-C₆-haloalkylsulfinyl is a C₁-C₆-haloalkyl radical as         mentioned above which is attached to the skeleton via a sulfinyl         group (—SO—);     -   C₃-C₆-haloalkenylsulfinyl is a C₃-C₆-haloalkenyl radical as         mentioned above which is attached to the skeleton via a sulfinyl         group (—SO—);     -   C₃-C₆-haloalkynylsulfinyl is a C₃-C₆-haloalkynyl radical as         mentioned above which is attached to the skeleton via a sulfinyl         group (—SO—);     -   C₁-C₆-haloalkylsulfonyl is a C₁-C₆-haloalkyl radical as         mentioned above which is attached to the skeleton via a sulfonyl         group (—SO₂—);     -   C₃-C₆-haloalkenylsulfonyl is a C₃-C₆-haloalkenyl radical as         mentioned above which is attached to the skeleton via a sulfonyl         group (—SO₂—);     -   C₃-C₆-haloalkynylsulfonyl is a C₃-C₆-haloalkynyl radical as         mentioned above which is attached to the skeleton via a sulfonyl         group (—SO₂—);     -   C₁-C₆-alkylcarbonyloxy is a C₁-C₆-alkyl radical which is         attached to the skeleton via a carbonyloxy group (—C(O)—O—) via         is the oxygen;     -   C₁-C₆-alkoxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as mentioned         above which is substituted by a C₁-C₆-alkoxy radical as         mentioned above, for example methoxymethyl, ethoxymethyl,         n-propoxymethyl, i-propoxymethyl, n-butoxymethyl,         (1-methylpropoxy)methyl, (2-methylpropoxy)methyl,         t-butoxymethyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,         2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl,         2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,         2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,         2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl,         2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl,         2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,         3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl,         3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl,         3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,         3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,         2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl,         2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,         2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,         3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl,         3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,         3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,         4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,         4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or         4-(1,1-dimethylethoxy)butyl;     -   C₃-C₆-alkenyloxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₃-C₆-alkenyloxy         radical as mentioned above;     -   C₃-C₄-alkynyloxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₃-C₄-alkynyloxy         radical as mentioned above;     -   C₁-C₆-alkylthio-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₁-C₆-alkylthio         radical as mentioned above;     -   C₃-C₆-alkenylthio-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₃-C₆-alkenylthio         radical as mentioned above;     -   C₃-C₄-alkynylthio-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₃-C₆-alkynylthio         radical as mentioned above;     -   C₁-C₆-alkylcarbonyl is a C₁-C₆-alkyl radical as mentioned above         which is attached to the skeleton via a carbonyl group (—CO—);     -   C₁-C₆-alkoxycarbonyl is a C₁-C₆-alkoxy radical as mentioned         above which is attached to the skeleton via a carbonyl group         (—CO—);     -   C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₁-C₆-alkylcarbonyl         radical as mentioned above;     -   C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl is a C₁-C₄-alkyl radical as         mentioned above which is substituted by a C₁-C₆-alkoxycarbonyl         radical as mentioned above;     -   C₁-C₆-alkoxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical which is         substituted by C₁-C₆-alkoxy as mentioned above, where the alkyl         radical is defined as mentioned above;     -   C₃-C₆-alkenyloxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical which is         substituted by C₃-C₆-alkenyloxy as mentioned above, where the         C₁-C₄-alkyl radical is defined as mentioned above;     -   C₃-C₆-alkynyloxy-C₁-C₄-alkyl is a C₁-C₄-alkyl radical which is         substituted by C₃-C₆-alkynyloxy as mentioned above, where the         C₁-C₄-alkyl radical is defined as mentioned above;     -   C₁-C₆-alkylthio-C₁-C₄-alkyl is a C₁-C₄-alkyl radical which is         substituted by C₁-C₆-alkylthio as mentioned above, where the         C₁-C₄-alkyl radical is defined as mentioned above;     -   C₁-C₆-alkoxy-C₁-C₄-alkoxy is a C₁-C₆-alkoxy radical which is         substituted by C₁-C₄-alkoxy as mentioned above, where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₃-C₆-alkenyloxy-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which is         substituted by C₃-C₆-alkenyloxy as mentioned above, where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₃-C₄-alkynyloxy-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which is         substituted by C₃-C₄-alkynyloxy as mentioned above, where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₁-C₆-alkylthio-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which is         substituted by C₁-C₆-alkylthio as mentioned above, where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₃-C₆-alkenylthio-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which         is substituted by C₃-C₆-alkenylthio as mentioned above where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₃-C₆-alkynylthio-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which         is substituted by C₃-C₆-alkynylthio as mentioned above where the         C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical which         is substituted by C₁-C₆-alkylcarbonyl as mentioned above where         the C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical         which is substituted by C₁-C₆-alkylcarbonyloxy as mentioned         above where the C₁-C₄-alkoxy radical is defined as mentioned         above;     -   C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy is a C₁-C₄-alkoxy radical         which is substituted by C₁-C₆-alkoxycarbonyl as mentioned above         where the C₁-C₄-alkoxy radical is defined as mentioned above;     -   C₃-C₄-alkylene is n-propylene (—CH₂CH₂CH₂—) or n-butylene         (—CH₂CH₂CH₂CH₂—);     -   C₃-C₄-alkenylene is a divalent unbranched chain of one or two         CH═CH— groups and/or one or two CH₂ groups in any position, for         example —CH═CHCH₂—, CH₂CH═CHCH₂, CH═CHCH₂CH₂ or CH═CH—CH═CH₂;     -   C₁-C₄-alkylamino is a C₁-C₄-alkyl radical as mentioned above         which is attached to the skeleton via an amino group (—NH—);     -   C₁-C₆-alkylamino is a C₁-C₆-alkyl radical as mentioned above         which is attached to the skeleton via an amino group (—NH—);     -   C₁-C₄-dialkylamino are two independent C₁-C₄-alkyl radicals as         mentioned above which are attached to the skeleton via a         nitrogen atom (>N—);     -   C₁-C₆-dialkylamino are two independent C₁-C₆-alkyl radicals as         mentioned above which are attached to the skeleton via a         nitrogen atom (>N—).

With respect to the use of the substituted phenylalanine derivatives I as herbicides, preference is given to those compounds I in which the substituents are as defined above, in each case on their own or in combination:

-   -   R¹ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,         C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₁-C₆-haloalkylsulfinyl,         C₃-C₆-haloalkenylsulfinyl, C₁-C₆-haloalkylsulfonyl or         C₃-C₆-haloalkenylsulfonyl;         -   preferably hydrogen, halogen, cyano, C₁-C₆-alkyl,             C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl;         -   particularly preferably hydrogen, cyano, halogen or C₁-C₆             alkyl;     -   R² is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl,         C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,         C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy or         C₃-C₆-halogenalkynyloxy;         -   preferably hydrogen, halogen, cyano, C₁-C₆-haloalkyl or             C₁-C₆-alkyl;         -   particularly preferably hydrogen or C₁-C₆-haloalkyl;         -   furthermore particularly preferably halogen or C₁-C₆-alkyl;         -   very particularly preferably hydrogen, halogen or             C₁-C₆-alkyl;     -   R³ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;         preferably hydrogen or halogen;     -   R⁴ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,         C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy;         -   preferably hydrogen, halogen, C₁-C₆-alkyl or             C₁-C₆-haloalkyl;         -   particularly preferably hydrogen or halogen;         -   very particularly preferably hydrogen;     -   R⁵ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl,         C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy,         C₃-C₆-alkynyloxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or         C₃-C₆-haloalkenyloxy; preferably hydrogen, halogen, C₁-C₆-alkyl         or C₁-C₆-haloalkyl, particularly preferably hydrogen;         -   likewise particularly preferably C₁-C₆-alkyl or halogen;     -   R⁶ is hydrogen or C₁-C₆-alkyl;     -   R⁷ is hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl or C₁-C₆-haloalkyl;         -   preferably hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or             C₂-C₆-alkynyl;         -   particularly preferably also C₁-C₆-alkyl or hydrogen;     -   R⁸ is methyl or methoxy;         -   likewise hydroxyl;     -   R⁹ is hydrogen or methyl;         -   preferably hydrogen;         -   when R⁸ is hydroxyl, preferably methyl;     -   R¹⁰ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl,         C₁-C₄-haloalkoxycarbonyl;         -   preferably hydrogen;     -   R¹¹ is halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy,         C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio,         C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl or CO—R¹⁶;         -   preferably halogen, cyano, C₁-C₆-alkylthio,             C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkyl,             C₁-c₆-haloalkyl or CO—R¹⁶;         -   in addition preferably C₁-C₆-haloalkoxy,             C₁-C₆-haloalkylthio;         -   particularly preferably halogen, cyano, C₁-C₆-alkylthio,         -   C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkyl or             C₁-C₆-haloalkyl;         -   likewise particularly preferably C₁-C₆-haloalkoxy,             C₁-C₆-haloalkylthio;         -   very particularly preferably halogen or C₁-C₆-haloalkyl,             where the halogen substituent in C₁-C₆-haloalkyl is             preferably fluorine;         -   furthermore very particularly preferably C₁-C₆-haloalkoxy,             C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl or             C₁-C₆-alkylsulfinyl, where the halogen substituent in             C₁-C₆-haloalkyl, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl or             C₁-C₆-alkylsulfinyl is preferably fluorine;     -   R¹³ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl or CO—R¹⁶;         -   preferably hydrogen, halogen, cyano, C₁-C₆-alkyl,             C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,             C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or             C₁-C₆-haloalkylthio or CO—R¹⁶;         -   particularly preferably hydrogen, halogen, cyano,             C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,             C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl,             C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio;         -   very particularly preferably halogen, such as, for example,             chlorine and fluorine, C₁-C₆-alkyl, C₁-C₆-haloalkyl, where             the halogen substituent in C₁-C₆-haloalkyl is preferably             fluorine;         -   likewise very particularly preferably hydrogen;     -   R¹² and R¹⁴ are hydrogen, halogen, cyano, C₁-C₆-alkyl,         C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl, or CO—R¹⁶;         -   preferably hydrogen, halogen, cyano, C₁-C₆-alkyl,             C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,             C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,             C₁-C₆-haloalkylthio or CO—R¹⁶;         -   particularly preferably hydrogen, halogen, cyano,             C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,             C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl,             C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio;         -   R¹² is very particularly preferably hydrogen or halogen,             such as, for example, chlorine and fluorine, C₁-C₆-alkyl,             C₁-C₆-haloalkyl, where the halogen substituent in             C₁-C₆-haloalkyl is preferably fluorine;     -   R¹² is furthermore very particularly preferably cyano,         C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio, where the halogen         substituent in C₁-C₆-haloalkyl or C₁-C₆-haloalkylthio is         preferably fluorine;     -   R¹⁴ is furthermore very particularly preferably hydrogen;     -   R¹⁵ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;         -   preferably hydrogen; and     -   R¹⁶ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-Alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylamino or         di(C₁-C₆-alkyl)amino, preferably C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylamino or         di(C₁-C₆-alkyl)amino.

Preference is furthermore given to phenylalanine derivatives of the formula I where in each case independently of one another

-   -   R¹ is hydrogen, halogen, such as fluorine, chlorine or bromine,         cyano, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl or         isopropyl;         -   preferably hydrogen, fluorine, methyl;         -   furthermore preferably chlorine or ethyl;     -   R² is hydrogen, C₁-C₄-haloalkyl, such as fluoromethyl,         difluoromethyl or trifluoromethyl, halogen, such as fluorine,         chlorine or bromine;         -   likewise C₁-C₄-alkyl such as methyl, ethyl, n-propyl or             isopropyl;         -   preferably hydrogen or C₁-C₄-alkyl, such as methyl, ethyl,             n-propyl or isopropyl;         -   in addition preferably fluorine, chlorine or bromine;         -   particularly preferably hydrogen, fluorine, chlorine or             methyl;     -   R³ is hydrogen, halogen, such as fluorine, chlorine or bromine,         C₁-C₄-alkyl, such as methyl, ethyl, n-propyl or isopropyl;         -   preferably hydrogen, fluorine, chlorine or bromine;         -   furthermore preferably methyl;         -   particularly preferably hydrogen, fluorine or chlorine;     -   R⁴ is hydrogen, C₁-C₄-haloalkyl, such as fluoromethyl,         difluoromethyl or trifluoromethyl, halogen, such as fluorine,         chlorine or bromine, C₁-C₄-alkyl, such as methyl, ethyl,         n-propyl or isopropyl;         -   preferably hydrogen;     -   R⁵ is hydrogen, C₁-C₄-haloalkyl such as fluoromethyl,         difluoromethyl or trifluoromethyl, halogen, such as fluorine,         chlorine or bromine, C₁-C₄-alkyl, such as methyl, ethyl,         n-propyl or isopropyl;         -   preferably hydrogen;         -   in addition preferably fluorine, chlorine or methyl.

Preference is furthermore given to phenylalanine derivatives of the formula I where in each case independently of one another

-   -   R⁷ is hydrogen, haloalkyl, such as fluoromethyl, difluoromethyl         or trifluoromethyl, halogen, such as fluorine, chlorine or         bromine, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl or         isopropyl, or C₂-C₄-alkenyl, such as ethenyl, prop-1-en-1-yl,         1-methylethenyl, but-1-en-1-yl, but-1-en-2-yl,         1-methylprop-1-en-1-yl or 2-methylprop-1-en-1-yl, C₂-C₄-alkynyl,         such as ethynyl, prop-1-yn-1-yl or n-but-l-yn-1-yl;     -   preferably hydrogen, C₁-C₄-alkyl, such as methyl or ethyl, or         C₂-C₄-alkenyl, such as ethenyl, prop-1-en-1-yl, 1-methylethenyl,         but-1-en-1-yl, but-1-en-2-yl, 1-methylprop-1-en-1-yl or         2-methylprop-1-en-1-yl;         -   particularly preferably hydrogen or methyl;         -   furthermore particularly preferably ethyl; and     -   R⁶ is hydrogen.

Preference is furthermore given to phenylalanine derivatives of the formula I where R¹⁰ is hydrogen.

Preference is is furthermore given to phenylalanine derivatives of the formula I where in each case independently of one another

-   -   R⁸ is C₁-C₆-alkoxy or hydroxyl and     -   R⁹ is hydrogen, C₁-C₆-alkyl, preferably methyl.

Preference is also given to compounds I in which

-   -   R⁸ is methyl or ethyl, preferably methyl, and     -   R⁹ is hydrogen or C₁-C₆-alkyl, preferably hydrogen.

Particular preference is given to compounds I in which

-   -   R⁸ is C₁-C₄-alkoxy, C₁-C₄-alkyl or hydroxyl;         -   preferably methoxy, methyl or hydroxyl;     -   R⁹ is hydrogen, C₁-C₆-alkyl, preferably hydrogen or methyl.

In this case, R⁹ is then preferably methyl, if R⁸ is hydroxyl.

Preference is also given to compounds I in which

-   -   R⁸ is methyl and     -   R⁹ is hydrogen.

Preference is furthermore given to phenylalanine derivatives of the formula I where in each case independently of one another

-   -   R¹¹ is cyano, C₁-C₄-alkyl, such as methyl, ethyl, n-propyl or         isopropyl, C₁-C₄-haloalkyl, such as fluoromethyl, difluoromethyl         or trifluoromethyl, halogen, such as fluorine, chlorine or         bromine, C₁-C₄-alkylsulfonyl, such as methylsulfonyl,         ethylsulfonyl, n-propylsulfonyl or isopropylsulfonyl, or CO—R¹⁶;         -   in addition C₁-C₄-haloalkoxy, such as fluoromethoxy,             difluoromethoxy, trifluoromethoxy, or C₁-C₄-haloalkylthio,             such as fluorothiomethyl, difluorothiomethyl or             trifluorothiomethyl, or C₁-C₄-alkylsulfinyl, such as             methylsulfinyl, ethylsulfinyl, n-propylsulfinyl or             isopropylsulfinyl;         -   preferably cyano, C₁-C₄-alkyl, such as methyl, ethyl,             n-propyl or isopropyl, C₁-C₄-haloalkyl, such as             fluoromethyl, difluoromethyl or trifluoromethyl, halogen,             such as fluorine, chlorine or bromine, C₁-C₄-alkylsulfonyl,             such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or             isopropylsulfonyl;         -   likewise preferably C₁-C₄-haloalkoxy, such as fluoromethoxy,             difluoromethoxy, or trifluoromethoxy, or             C₁-C₄-haloalkylthio, such as fluorothiomethyl,             difluorothiomethyl or trifluorothiomethyl, or             C₁-C₄-alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl,             n-propylsulfinyl or isopropylsulfinyl;         -   particularly preferably trifluoromethyl, chlorine, bromine;         -   furthermore particularly preferably fluorine, fluoromethyl,             difluoromethyl, fluoromethoxy, difluoromethoxy or             trifluoromethoxy, fluorothiomethyl, difluorothiomethyl or             trifluorothiomethyl, methylsulfonyl or methylsulfinyl;     -   R¹², R¹³ and R¹⁴ are hydrogen, cyano, halogen, such as fluorine,         chlorine or bromine, C₁-C₄-haloalkyl, such as fluoromethyl,         difluoromethyl or trifluoromethyl, C₁-C₄-alkyl, such as methyl,         ethyl, n-propyl or isopropyl, C₁-C₄-alkylsulfonyl, such as         methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or         isopropylsulfonyl, C₁-C₄-alkoxy, such as methoxy, ethoxy,         n-propoxy or isopropoxy, halomethoxy, such as fluoromethoxy,         difluoromethoxy or trifluoromethoxy, or CO—R¹⁶;         -   furthermore halomethylthio, such as fluorothiomethyl,             difluorothiomethyl or trifluorothiomethyl;         -   preferably hydrogen, cyano, halogen, such as fluorine,             chlorine or bromine, C₁-C₄-haloalkyl, such as fluoromethyl,             difluoromethyl or trifluoromethyl, C₁-C₄-alkyl, such as             methyl, ethyl, n-propyl or isopropyl, C₁-C₄-alkylsulfonyl,             such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl or             isopropylsulfonyl, C₁-C₄-alkoxy, such as methoxy, ethoxy,             n-propoxy or isopropoxy, halomethoxy, such as fluoromethoxy,             difluoromethoxy or trifluoromethoxy;         -   furthermore halomethylthio, such as fluorothiomethyl,             difluorothiomethyl or trifluorothiomethyl;         -   particularly preferably hydrogen, halogen, such as fluorine             or chlorine, C₁-C₄-haloalkyl, such as fluoromethyl,             difluoromethyl or trifluoromethyl, C₁-C₄-alkyl, such as             methyl, ethyl, n-propyl or isopropyl;         -   likewise particularly preferably halomethoxy, such as             fluoromethoxy, difluoromethoxy or trifluoromethoxy,             halomethylthio, such as fluorothiomethyl,             difluorothiomethyl, or trifluorothiomethyl;     -   R¹² is very particularly preferably hydrogen, cyano, fluorine,         chlorine, methyl, fluoromethyl, difluoromethyl or         trifluoromethyl, fluoromethoxy, difluoromethoxy,         trifluoromethoxy, fluorothiomethyl, difluorothiomethyl,         trifluorothiomethyl,     -   R¹³ is very particularly preferably hydrogen, fluorine or         chlorine;     -   R¹⁴ is very particularly preferably hydrogen;     -   R¹⁵ is hydrogen; and     -   R¹⁶ is C₁-C₄-alkoxy, such as methoxy, ethoxy, n-propoxy,         isopropoxy, n-butoxy or t-butoxy, C₁-C₄-alkyl, such as methyl,         ethyl, n-propyl or isopropyl, C₁-alkyl, such as fluoromethyl,         difluoromethyl or trifluoromethyl, or C₁-haloalkoxy, such as         fluoromethoxy, difluoromethoxy or trifluoromethoxy.

Preference is also given to phenylalanine derivatives of the formula I in which the radicals

-   -   R¹, R², R⁴ and R⁵ are hydrogen, halogen, hydroxyl, mercapto,         nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy,         C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio,         C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy,         C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl,         C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,         C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl,         C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl,         C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy,         C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy,         C₃-C₆-alkynylthio-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy,         C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶;     -   R³ is hydrogen, mercapto, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₃-C₆-alkenylthio,         C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl,         C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl,         C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl,         C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkylthio,         C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio,         C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl,         C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl,         C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl,         C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-alkenyloxy-C₁-C₄-alkyl,         C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,         C₃-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₆-alkynylthio-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl,         C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,         C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl, or CO—R¹⁶.

Preference is also given to phenylalanine derivatives of the formula I in which R¹, R², R³, R⁴ and R⁵ are hydrogen.

Preference is also liven to phenylalanine derivatives of the formula I in which

-   -   R¹, R² and R³ in each case independentlly of one another are         hydrogen, fluorine, chlorine, methyl or trifluoromethyl;     -   R⁴, R⁵, R⁶, R⁹, R¹⁰ and R¹⁵ are hydrogen;     -   R⁷ is hydrogen or methyl;     -   R⁸ is methyl;     -   R¹¹, R¹², R¹³ and R¹⁴ in each case independently of one another         are hydrogen, bromine, methylsulfonyl, fluorine, chlorine,         methyl, trifluoromethyl, difluoromethyl, methoxy, cyano,         preferably H, fluorine, chlorine, methyl, trifluoromethyl,         difluoromethyl, ethoxy or cyano.

Particular preference is also given to phenylalanine derivatives of the formula I′ (R⁴, R⁶, R¹⁰, R¹⁴ and R¹⁵ are hydrogen) in which

-   -   R¹, R², R³, R⁵ in each case independently of one another are         hydrogen, fluorine, chlorine, methyl or ethyl;     -   R⁷ is hydrogen, methyl or ethyl;     -   R⁸ is methoxy, methyl or hydroxyl;     -   R⁹ is hydrogen;         -   is methyl if R⁸ is hydroxyl;     -   R¹¹ is fluorine, chlorine, halomethyl, such as fluoromethyl,         difluoromethyl, trifluoromethyl, halomethoxy, such as         fluoromethoxy, difluoromethoxy, trifluoromethoxy, halothioalkyl,         such as fluorothiomethyl, difluorothiomethyl,         trifluorothiomethyl, methylsulfinyl or methylsulfonyl;     -   R¹² is hydrogen, cyano, methyl, fluorine, chlorine, halomethyl,         such as fluoromethyl, difluoromethyl, trifluoromethyl,         halomethoxy, such as fluoromethoxy, difluoromethoxy,         trifluoromethoxy, halothioalkyl, such as fluorothiomethyl,         difluorothiomethyl, trifluorothiomethyl;     -   R¹³ is hydrogen, fluorine, chlorine.

In particular with a view to their use, preference is also given to the compounds I′ compiled in the tables below.

Table 1:

Compounds of the formula I′ (R⁴, R⁶, R¹⁰, R¹⁴ and R¹⁵ are hydrogen) in which R³ is H, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 2:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 3:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 4:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Tabelle 5:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 6:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 7:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 8:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 9:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 10:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 11:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 12:

Compounds of the formula I′, in which R³ is H, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 13:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 14:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 15:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 16:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 17:

Compounds of the formula II, in which R³ is H, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 18:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 19:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 20: Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 21:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 22:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 23:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 24:

Compounds of the formula I′, in which R³ is H, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 25:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 26:

Compounds of the formula II, in which R³ is H, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 27:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 28:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 29:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 30:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 31:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 32:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 33:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 34:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 35:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 36:

Compounds of the formula I′, in which R³ is H, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 37:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 38:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 39:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 40:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 41:

Compounds of the, formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 42:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 43:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 44:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 45:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 46:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 47:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 48:

Compounds of the formula I′, in which R³ is H, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 49:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 50:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 51:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 52:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 53:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 54:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 55:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 56:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 57:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 58:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 59:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 60:

Compounds of the formula I′, in which R³ is F, R⁵ is H, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 61:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 62:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 63:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 64:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 65:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 66:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 67:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 68:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 69:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 70:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 71:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 72:

Compounds of the formula I′, in which R³ is F, R⁵ is F, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 73:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 74:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 75:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 76:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 77:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 78:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 79:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 80:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 81:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 82:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 83:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 84:

Compounds of the formula I′, in which R³ is F, R⁵ is Cl, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 85:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 86:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 87:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is H, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 88:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is H, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 89:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 90:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 91:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 92:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 93:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is CH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 94:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OCH₃ and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 95:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is H and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A.

Table 96:

Compounds of the formula I′, in which R³ is F, R⁵ is CH₃, R⁷ is CH₂CH₃, R⁹ is CH₃ and R⁸ is OH and the combination of the substituents R¹, R², R¹¹, R¹² and R¹³ for a compound corresponds in each case to a row of table A. TABLE 1 No. R¹ R² R¹¹ R¹² R¹³ A-1 H H F H H A-2 F H F H H A-3 Cl H F H H A-4 CH₃ H F H H A-5 CH₂CH₃ H F H H A-6 H H Cl H H A-7 F H Cl H H A-8 Cl H Cl H H A-9 CH₃ H Cl H H A-10 CH₂CH₃ H Cl H H A-11 H H CHF₂ H H A-12 F H CHF₂ H H A-13 Cl H CHF₂ H H A-14 CH₃ H CHF₂ H H A-15 CH₂CH₃ H CHF₂ H H A-16 H H CF₃ H H A-17 F H CF₃ H H A-18 Cl H CF₃ H H A-19 CH₃ H CF₃ H H A-20 CH₂CH₃ H CF₃ H H A-21 H H SCHF₂ H H A-22 F H SCHF₂ H H A-23 Cl H SCHF₂ H H A-24 CH₃ H SCHF₂ H H A-25 CH₂CH₃ H SCHF₂ H H A-26 H H SCF₃ H H A-27 F H SCF₃ H H A-28 Cl H SCF₃ H H A-29 CH₃ H SCF₃ H H A-30 CH₂CH₃ H SCF₃ H H A-31 H H OCHF₂ H H A-32 F H OCHF₂ H H A-33 Cl H OCHF₂ H H A-34 CH₃ H OCHF₂ H H A-35 CH₂CH₃ H OCHF₂ H H A-36 H H OCF₃ H H A-37 F H OCF₃ H H A-38 Cl H OCF₃ H H A-39 CH₃ H OCF₃ H H A-40 CH₂CH₃ H OCF₃ H H A-41 H H F F H A-42 F H F F H A-43 Cl H F F H A-44 CH₃ H F F H A-45 CH₂CH₃ H F F H A-46 H H Cl F H A-47 F H Cl F H A-48 Cl H Cl F H A-49 CH₃ H Cl F H A-50 CH₂CH₃ H Cl F H A-51 H H CHF₂ F H A-52 F H CHF₂ F H A-53 Cl H CHF₂ F H A-54 CH₃ H CHF₂ F H A-55 CH₂CH₃ H CHF₂ F H A-56 H H CF₃ F H A-57 F H CF₃ F H A-58 Cl H CF₃ F H A-59 CH₃ H CF₃ F H A-60 CH₂CH₃ H CF₃ F H A-61 H H SCHF₂ F H A-62 F H SCHF₂ F H A-63 Cl H SCHF₂ F H A-64 CH₃ H SCHF₂ F H A-65 CH₂CH₃ H SCHF₂ F H A-66 H H SCF₃ F H A-67 F H SCF₃ F H A-68 Cl H SCF₃ F H A-69 CH₃ H SCF₃ F H A-70 CH₂CH₃ H SCF₃ F H A-71 H H OCHF₂ F H A-72 F H OCHF₂ F H A-73 Cl H OCHF₂ F H A-74 CH₃ H OCHF₂ F H A-75 CH₂CH₃ H OCHF₂ F H A-76 H H OCF₃ F H A-77 F H OCF₃ F H A-78 Cl H OCF₃ F H A-79 CH₃ H OCF₃ F H A-80 CH₂CH₃ H OCF₃ F H A-81 H H F Cl H A-82 F H F Cl H A-83 Cl H F Cl H A-84 CH₃ H F Cl H A-85 CH₂CH₃ H F Cl H A-86 H H Cl Cl H A-87 F H Cl Cl H A-88 Cl H Cl Cl H A-89 CH₃ H Cl Cl H A-90 CH₂CH₃ H Cl Cl H A-91 H H CHF₂ Cl H A-92 F H CHF₂ Cl H A-93 Cl H CHF₂ Cl H A-94 CH₃ H CHF₂ Cl H A-95 CH₂CH₃ H CHF₂ Cl H A-96 H H CF₃ Cl H A-97 F H CF₃ Cl H A-98 Cl H CF₃ Cl H A-99 CH₃ H CF₃ Cl H A-100 CH₂CH₃ H CF₃ Cl H A-101 H H SCHF₂ Cl H A-102 F H SCHF₂ Cl H A-103 Cl H SCHF₂ Cl H A-104 CH₃ H SCHF₂ Cl H A-105 CH₂CH₃ H SCHF₂ Cl H A-106 H H SCF₃ Cl H A-107 F H SCF₃ Cl H A-108 Cl H SCF₃ Cl H A-109 CH₃ H SCF₃ Cl H A-110 CH₂CH₃ H SCF₃ Cl H A-111 H H OCHF₂ Cl H A-112 F H OCHF₂ Cl H A-113 Cl H OCHF₂ Cl H A-114 CH₃ H OCHF₂ Cl H A-115 CH₂CH₃ H OCHF₂ Cl H A-116 H H OCF₃ Cl H A-117 F H OCF₃ Cl H A-118 Cl H OCF₃ Cl H A-119 CH₃ H OCF₃ Cl H A-120 CH₂CH₃ H OCF₃ Cl H A-121 H H F CHF₂ H A-122 F H F CHF₂ H A-123 Cl H F CHF₂ H A-124 CH₃ H F CHF₂ H A-125 CH₂CH₃ H F CHF₂ H A-126 H H Cl CHF₂ H A-127 F H Cl CHF₂ H A-128 Cl H Cl CHF₂ H A-129 CH₃ H Cl CHF₂ H A-130 CH₂CH₃ H Cl CHF₂ H A-131 H H CHF2 CHF₂ H A-132 F H CHF2 CHF₂ H A-133 Cl H CHF2 CHF₂ H A-134 CH₃ H CHF2 CHF₂ H A-135 CH₂CH₃ H CHF2 CHF₂ H A-136 H H CF₃ CHF₂ H A-137 F H CF₃ CHF₂ H A-138 Cl H CF₃ CHF₂ H A-139 CH₃ H CF₃ CHF₂ H A-140 CH₂CH₃ H CF₃ CHF₂ H A-141 H H SCHF₂ CHF₂ H A-142 F H SCHF₂ CHF₂ H A-143 Cl H SCHF₂ CHF₂ H A-144 CH₃ H SCHF₂ CHF₂ H A-145 CH₂CH₃ H SCHF₂ CHF₂ H A-146 H H SCF₃ CHF₂ H A-147 F H SCF₃ CHF₂ H A-148 Cl H SCF₃ CHF₂ H A-149 CH₃ H SCF₃ CHF₂ H A-150 CH₂CH₃ H SCF₃ CHF₂ H A-151 H H OCHF₂ CHF₂ H A-152 F H OCHF₂ CHF₂ H A-153 Cl H OCHF₂ CHF₂ H A-154 CH₃ H OCHF₂ CHF₂ H A-155 CH₂CH₃ H OCHF₂ CHF₂ H A-156 H H OCF₃ CHF₂ H A-157 F H OCF₃ CHF₂ H A-158 Cl H OCF₃ CHF₂ H A-159 CH₃ H OCF₃ CHF₂ H A-160 CH₂CH₃ H OCF₃ CHF₂ H A-161 H H F CF₃ H A-162 F H F CF₃ H A-163 Cl H F CF₃ H A-164 CH₃ H F CF₃ H A-165 CH₂CH₃ H F CF₃ H A-166 H H Cl CF₃ H A-167 F H Cl CF₃ H A-168 Cl H Cl CF₃ H A-169 CH₃ H Cl CF₃ H A-170 CH₂CH₃ H Cl CF₃ H A-171 H H CHF2 CF₃ H A-172 F H CHF2 CF₃ H A-173 Cl H CHF2 CF₃ H A-174 CH₃ H CHF2 CF₃ H A-175 CH₂CH₃ H CHF2 CF₃ H A-176 H H CF₃ CF₃ H A-177 F H CF₃ CF₃ H A-178 Cl H CF₃ CF₃ H A-179 CH₃ H CF₃ CF₃ H A-180 CH₂CH₃ H CF₃ CF₃ H A-181 H H SCHF₂ CF₃ H A-182 F H SCHF₂ CF₃ H A-183 Cl H SCHF₂ CF₃ H A-184 CH₃ H SCHF₂ CF₃ H A-185 CH₂CH₃ H SCHF₂ CF₃ H A-186 H H SCF₃ CF₃ H A-187 F H SCF₃ CF₃ H A-188 Cl H SCF₃ CF₃ H A-189 CH₃ H SCF₃ CF₃ H A-190 CH₂CH₃ H SCF₃ CF₃ H A-191 H H OCHF₂ CF₃ H A-192 F H OCHF₂ CF₃ H A-193 Cl H OCHF₂ CF₃ H A-194 CH₃ H OCHF₂ CF₃ H A-195 CH₂CH₃ H OCHF₂ CF₃ H A-196 H H OCF₃ CF₃ H A-197 F H OCF₃ CF₃ H A-198 Cl H OCF₃ CF₃ H A-199 CH₃ H OCF₃ CF₃ H A-200 CH₂CH₃ H OCF₃ CF₃ H A-201 H H F H F A-202 F H F H F A-203 Cl H F H F A-204 CH₃ H F H F A-205 CH₂CH₃ H F H F A-206 H H Cl H F A-207 F H Cl H F A-208 Cl H Cl H F A-209 CH₃ H Cl H F A-210 CH₂CH₃ H Cl H F A-211 H H CHF2 H F A-212 F H CHF2 H F A-213 Cl H CHF2 H F A-214 CH₃ H CHF2 H F A-215 CH₂CH₃ H CHF2 H F A-216 H H CF₃ H F A-217 F H CF₃ H F A-218 Cl H CF₃ H F A-219 CH₃ H CF₃ H F A-220 CH₂CH₃ H CF₃ H F A-221 H H SCHF₂ H F A-222 F H SCHF₂ H F A-223 Cl H SCHF₂ H F A-224 CH₃ H SCHF₂ H F A-225 CH₂CH₃ H SCHF₂ H F A-226 H H SCF₃ H F A-227 F H SCF₃ H F A-228 Cl H SCF₃ H F A-229 CH₃ H SCF₃ H F A-230 CH₂CH₃ H SCF₃ H F A-231 H H OCHF₂ H F A-232 F H OCHF₂ H F A-233 Cl H OCHF₂ H F A-234 CH₃ H OCHF₂ H F A-235 CH₂CH₃ H OCHF₂ H F A-236 H H OCF₃ H F A-237 F H OCF₃ H F A-238 Cl H OCF₃ H F A-239 CH₃ H OCF₃ H F A-240 CH₂CH₃ H OCF₃ H F A-241 H H F F F A-242 F H F F F A-243 Cl H F F F A-244 CH₃ H F F F A-245 CH₂CH₃ H F F F A-246 H H Cl F F A-247 F H Cl F F A-248 Cl H Cl F F A-249 CH₃ H Cl F F A-250 CH₂CH₃ H Cl F F A-251 H H CHF2 F F A-252 F H CHF2 F F A-253 Cl H CHF2 F F A-254 CH₃ H CHF2 F F A-255 CH₂CH₃ H CHF2 F F A-256 H H CF₃ F F A-257 F H CF₃ F F A-258 Cl H CF₃ F F A-259 CH₃ H CF₃ F F A-260 CH₂CH₃ H CF₃ F F A-261 H H SCHF₂ F F A-262 F H SCHF₂ F F A-263 Cl H SCHF₂ F F A-264 CH₃ H SCHF₂ F F A-265 CH₂CH₃ H SCHF₂ F F A-266 H H SCF₃ F F A-267 F H SCF₃ F F A-268 Cl H SCF₃ F F A-269 CH₃ H SCF₃ F F A-270 CH₂CH₃ H SCF₃ F F A-271 H H OCHF₂ F F A-272 F H OCHF₂ F F A-273 Cl H OCHF₂ F F A-274 CH₃ H OCHF₂ F F A-275 CH₂CH₃ H OCHF₂ F F A-276 H H OCF₃ F F A-277 F H OCF₃ F F A-278 Cl H OCF₃ F F A-279 CH₃ H OCF₃ F F A-280 CH₂CH₃ H OCF₃ F F A-281 H H F Cl F A-282 F H F Cl F A-283 Cl H F Cl F A-284 CH₃ H F Cl F A-285 CH₂CH₃ H F Cl F A-286 H H Cl Cl F A-287 F H Cl Cl F A-288 Cl H Cl Cl F A-289 CH₃ H Cl Cl F A-290 CH₂CH₃ H Cl Cl F A-291 H H CHF2 Cl F A-292 F H CHF2 Cl F A-293 Cl H CHF2 Cl F A-294 CH₃ H CHF2 Cl F A-295 CH₂CH₃ H CHF2 Cl F A-296 H H CF₃ Cl F A-297 F H CF₃ Cl F A-298 Cl H CF₃ Cl F A-299 CH₃ H CF₃ Cl F A-300 CH₂CH₃ H CF₃ Cl F A-301 H H SCHF₂ Cl F A-302 F H SCHF₂ Cl F A-303 Cl H SCHF₂ Cl F A-304 CH₃ H SCHF₂ Cl F A-305 CH₂CH₃ H SCHF₂ Cl F A-306 H H SCF₃ Cl F A-307 F H SCF₃ Cl F A-308 Cl H SCF₃ Cl F A-309 CH₃ H SCF₃ Cl F A-310 CH₂CH₃ H SCF₃ Cl F A-311 H H OCHF₂ Cl F A-312 F H OCHF₂ Cl F A-313 Cl H OCHF₂ Cl F A-314 CH₃ H OCHF₂ Cl F A-315 CH₂CH₃ H OCHF₂ Cl F A-316 H H OCF₃ Cl F A-317 F H OCF₃ Cl F A-318 Cl H OCF₃ Cl F A-319 CH₃ H OCF₃ Cl F A-320 CH₂CH₃ H OCF₃ Cl F A-321 H H F CHF₂ F A-322 F H F CHF₂ F A-323 Cl H F CHF₂ F A-324 CH₃ H F CHF₂ F A-325 CH₂CH₃ H F CHF₂ F A-326 H H Cl CHF₂ F A-327 F H Cl CHF₂ F A-328 Cl H Cl CHF₂ F A-329 CH₃ H Cl CHF₂ F A-330 CH₂CH₃ H Cl CHF₂ F A-331 H H CHF2 CHF₂ F A-332 F H CHF2 CHF₂ F A-333 Cl H CHF2 CHF₂ F A-334 CH₃ H CHF2 CHF₂ F A-335 CH₂CH₃ H CHF2 CHF₂ F A-336 H H CF₃ CHF₂ F A-337 F H CF₃ CHF₂ F A-338 Cl H CF₃ CHF₂ F A-339 CH₃ H CF₃ CHF₂ F A-340 CH₂CH₃ H CF₃ CHF₂ F A-341 H H SCHF₂ CHF₂ F A-342 F H SCHF₂ CHF₂ F A-343 Cl H SCHF₂ CHF₂ F A-344 CH₃ H SCHF₂ CHF₂ F A-345 CH₂CH₃ H SCHF₂ CHF₂ F A-346 H H SCF₃ CHF₂ F A-347 F H SCF₃ CHF₂ F A-348 Cl H SCF₃ CHF₂ F A-349 CH₃ H SCF₃ CHF₂ F A-350 CH₂CH₃ H SCF₃ CHF₂ F A-351 H H OCHF₂ CHF₂ F A-352 F H OCHF₂ CHF₂ F A-353 Cl H OCHF₂ CHF₂ F A-354 CH₃ H OCHF₂ CHF₂ F A-355 CH₂CH₃ H OCHF₂ CHF₂ F A-356 H H OCF₃ CHF₂ F A-357 F H OCF₃ CHF₂ F A-358 Cl H OCF₃ CHF₂ F A-359 CH₃ H OCF₃ CHF₂ F A-360 CH₂CH₃ H OCF₃ CHF₂ F A-361 H H F CF₃ F A-362 F H F CF₃ F A-363 Cl H F CF₃ F A-364 CH₃ H F CF₃ F A-365 CH₂CH₃ H F CF₃ F A-366 H H Cl CF₃ F A-367 F H Cl CF₃ F A-368 Cl H Cl CF₃ F A-369 CH₃ H Cl CF₃ F A-370 CH₂CH₃ H Cl CF₃ F A-371 H H CHF2 CF₃ F A-372 F H CHF2 CF₃ F A-373 Cl H CHF2 CF₃ F A-374 CH₃ H CHF2 CF₃ F A-375 CH₂CH₃ H CHF2 CF₃ F A-376 H H CF₃ CF₃ F A-377 F H CF₃ CF₃ F A-378 Cl H CF₃ CF₃ F A-379 CH₃ H CF₃ CF₃ F A-380 CH₂CH₃ H CF₃ CF₃ F A-381 H H SCHF₂ CF₃ F A-382 F H SCHF₂ CF₃ F A-383 Cl H SCHF₂ CF₃ F A-384 CH₃ H SCHF₂ CF₃ F A-385 CH₂CH₃ H SCHF₂ CF₃ F A-386 H H SCF₃ CF₃ F A-387 F H SCF₃ CF₃ F A-388 Cl H SCF₃ CF₃ F A-389 CH₃ H SCF₃ CF₃ F A-390 CH₂CH₃ H SCF₃ CF₃ F A-391 H H OCHF₂ CF₃ F A-392 F H OCHF₂ CF₃ F A-393 Cl H OCHF₂ CF₃ F A-394 CH₃ H OCHF₂ CF₃ F A-395 CH₂CH₃ H OCHF₂ CF₃ F A-396 H H OCF₃ CF₃ F A-397 F H OCF₃ CF₃ F A-398 Cl H OCF₃ CF₃ F A-399 CH₃ H OCF₃ CF₃ F A-400 CH₂CH₃ H OCF₃ CF₃ F A-401 H H F H Cl A-402 F H F H Cl A-403 Cl H F H Cl A-404 CH₃ H F H Cl A-405 CH₂CH₃ H F H Cl A-406 H H Cl H Cl A-407 F H Cl H Cl A-408 Cl H Cl H Cl A-409 CH₃ H Cl H Cl A-410 CH₂CH₃ H Cl H Cl A-411 H H CHF2 H Cl A-412 F H CHF2 H Cl A-413 Cl H CHF2 H Cl A-414 CH₃ H CHF2 H Cl A-415 CH₂CH₃ H CHF2 H Cl A-416 H H CF₃ H Cl A-417 F H CF₃ H Cl A-418 Cl H CF₃ H Cl A-419 CH₃ H CF₃ H Cl A-420 CH₂CH₃ H CF₃ H Cl A-421 H H SCHF₂ H Cl A-422 F H SCHF₂ H Cl A-423 Cl H SCHF₂ H Cl A-424 CH₃ H SCHF₂ H Cl A-425 CH₂CH₃ H SCHF₂ H Cl A-426 H H SCF₃ H Cl A-427 F H SCF₃ H Cl A-428 Cl H SCF₃ H Cl A-429 CH₃ H SCF₃ H Cl A-430 CH₂CH₃ H SCF₃ H Cl A-431 H H OCHF₂ H Cl A-432 F H OCHF₂ H Cl A-433 Cl H OCHF₂ H Cl A-434 CH₃ H OCHF₂ H Cl A-435 CH₂CH₃ H OCHF₂ H Cl A-436 H H OCF₃ H Cl A-437 F H OCF₃ H Cl A-438 Cl H OCF₃ H Cl A-439 CH₃ H OCF₃ H Cl A-440 CH₂CH₃ H OCF₃ H Cl A-441 H H F F Cl A-442 F H F F Cl A-443 Cl H F F Cl A-444 CH₃ H F F Cl A-445 CH₂CH₃ H F F Cl A-446 H H Cl F Cl A-447 F H Cl F Cl A-448 Cl H Cl F Cl A-449 CH₃ H Cl F Cl A-450 CH₂CH₃ H Cl F Cl A-451 H H CHF2 F Cl A-452 F H CHF2 F Cl A-453 Cl H CHF2 F Cl A-454 CH₃ H CHF2 F Cl A-455 CH₂CH₃ H CHF2 F Cl A-456 H H CF₃ F Cl A-457 F H CF₃ F Cl A-458 Cl H CF₃ F Cl A-459 CH₃ H CF₃ F Cl A-460 CH₂CH₃ H CF₃ F Cl A-461 H H SCHF₂ F Cl A-462 F H SCHF₂ F Cl A-463 Cl H SCHF₂ F Cl A-464 CH₃ H SCHF₂ F Cl A-465 CH₂CH₃ H SCHF₂ F Cl A-466 H H SCF₃ F Cl A-467 F H SCF₃ F Cl A-468 Cl H SCF₃ F Cl A-469 CH₃ H SCF₃ F Cl A-470 CH₂CH₃ H SCF₃ F Cl A-471 H H OCHF₂ F Cl A-472 F H OCHF₂ F Cl A-473 Cl H OCHF₂ F Cl A-474 CH₃ H OCHF₂ F Cl A-475 CH₂CH₃ H OCHF₂ F Cl A-476 H H OCF₃ F Cl A-477 F H OCF₃ F Cl A-478 Cl H OCF₃ F Cl A-479 CH₃ H OCF₃ F Cl A-480 CH₂CH₃ H OCF₃ F Cl A-481 H H F Cl Cl A-482 F H F Cl Cl A-483 Cl H F Cl Cl A-484 CH₃ H F Cl Cl A-485 CH₂CH₃ H F Cl Cl A-486 H H Cl Cl Cl A-487 F H Cl Cl Cl A-488 Cl H Cl Cl Cl A-489 CH₃ H Cl Cl Cl A-490 CH₂CH₃ H Cl Cl Cl A-491 H H CHF2 Cl Cl A-492 F H CHF2 Cl Cl A-493 Cl H CHF2 Cl Cl A-494 CH₃ H CHF2 Cl Cl A-495 CH₂CH₃ H CHF2 Cl Cl A-496 H H CF₃ Cl Cl A-497 F H CF₃ Cl Cl A-498 Cl H CF₃ Cl Cl A-499 CH₃ H CF₃ Cl Cl A-500 CH₂CH₃ H CF₃ Cl Cl A-501 H H SCHF₂ Cl Cl A-502 F H SCHF₂ Cl Cl A-503 Cl H SCHF₂ Cl Cl A-504 CH₃ H SCHF₂ Cl Cl A-505 CH₂CH₃ H SCHF₂ Cl Cl A-506 H H SCF₃ Cl Cl A-507 F H SCF₃ Cl Cl A-508 Cl H SCF₃ Cl Cl A-509 CH₃ H SCF₃ Cl Cl A-510 CH₂CH₃ H SCF₃ Cl Cl A-511 H H OCHF₂ Cl Cl A-512 F H OCHF₂ Cl Cl A-513 Cl H OCHF₂ Cl Cl A-514 CH₃ H OCHF₂ Cl Cl A-515 CH₂CH₃ H OCHF₂ Cl Cl A-516 H H OCF₃ Cl Cl A-517 F H OCF₃ Cl Cl A-518 Cl H OCF₃ Cl Cl A-519 CH₃ H OCF₃ Cl Cl A-520 CH₂CH₃ H OCF₃ Cl Cl A-521 H H F CHF₂ Cl A-522 F H F CHF₂ Cl A-523 Cl H F CHF₂ Cl A-524 CH₃ H F CHF₂ Cl A-525 CH₂CH₃ H F CHF₂ Cl A-526 H H Cl CHF₂ Cl A-527 F H Cl CHF₂ Cl A-528 Cl H Cl CHF₂ Cl A-529 CH₃ H Cl CHF₂ Cl A-530 CH₂CH₃ H Cl CHF₂ Cl A-531 H H CHF₂ CHF2 Cl A-532 F H CHF₂ CHF2 Cl A-533 Cl H CHF₂ CHF2 Cl A-534 CH₃ H CHF₂ CHF2 Cl A-535 CH₂CH₃ H CHF2 CHF₂ Cl A-536 H H CF₃ CHF₂ Cl A-537 F H CF₃ CHF₂ Cl A-538 Cl H CF₃ CHF₂ Cl A-539 CH₃ H CF₃ CHF₂ Cl A-540 CH₂CH₃ H CF₃ CHF₂ Cl A-541 H H SCHF₂ CHF₂ Cl A-542 F H SCHF₂ CHF₂ Cl A-543 Cl H SCHF₂ CHF₂ Cl A-544 CH₃ H SCHF₂ CHF₂ Cl A-545 CH₂CH₃ H SCHF₂ CHF₂ Cl A-546 H H SCF₃ CHF₂ Cl A-547 F H SCF₃ CHF₂ Cl A-548 Cl H SCF₃ CHF₂ Cl A-549 CH₃ H SCF₃ CHF₂ Cl A-550 CH₂CH₃ H SCF₃ CHF₂ Cl A-551 H H OCHF₂ CHF₂ Cl A-552 F H OCHF₂ CHF₂ Cl A-553 Cl H OCHF₂ CHF₂ Cl A-554 CH₃ H OCHF₂ CHF₂ Cl A-555 CH₂CH₃ H OCHF₂ CHF₂ Cl A-556 H H OCF₃ CHF₂ Cl A-557 F H OCF₃ CHF₂ Cl A-558 Cl H OCF₃ CHF₂ Cl A-559 CH₃ H OCF₃ CHF₂ Cl A-560 CH₂CH₃ H OCF₃ CHF₂ Cl A-561 H H F CF₃ Cl A-562 F H F CF₃ Cl A-563 Cl H F CF₃ Cl A-564 CH₃ H F CF₃ Cl A-565 CH₂CH₃ H F CF₃ Cl A-566 H H Cl CF₃ Cl A-567 F H Cl CF₃ Cl A-568 Cl H Cl CF₃ Cl A-569 CH₃ H Cl CF₃ Cl A-570 CH₂CH₃ H Cl CF₃ Cl A-571 H H CHF2 CF₃ Cl A-572 F H CHF2 CF₃ Cl A-573 Cl H CHF2 CF₃ Cl A-574 CH₃ H CHF2 CF₃ Cl A-575 CH₂CH₃ H CHF2 CF₃ Cl A-576 H H CF₃ CF₃ Cl A-577 F H CF₃ CF₃ Cl A-578 Cl H CF₃ CF₃ Cl A-579 CH₃ H CF₃ CF₃ Cl A-580 CH₂CH₃ H CF₃ CF₃ Cl A-581 H H SCHF₂ CF₃ Cl A-582 F H SCHF₂ CF₃ Cl A-583 Cl H SCHF₂ CF₃ Cl A-584 CH₃ H SCHF₂ CF₃ Cl A-585 CH₂CH₃ H SCHF₂ CF₃ Cl A-586 H H SCF₃ CF₃ Cl A-587 F H SCF₃ CF₃ Cl A-588 Cl H SCF₃ CF₃ Cl A-589 CH₃ H SCF₃ CF₃ Cl A-590 CH₂CH₃ H SCF₃ CF₃ Cl A-591 H H OCHF₂ CF₃ Cl A-592 F H OCHF₂ CF₃ Cl A-593 Cl H OCHF₂ CF₃ Cl A-594 CH₃ H OCHF₂ CF₃ Cl A-595 CH₂CH₃ H OCHF₂ CF₃ Cl A-596 H H OCF₃ CF₃ Cl A-597 F H OCF₃ CF₃ Cl A-598 Cl H OCF₃ CF₃ Cl A-599 CH₃ H OCF₃ CF₃ Cl A-600 CH₂CH₃ H OCF₃ CF₃ Cl A-601 H F F H H A-602 F F F H H A-603 Cl F F H H A-604 CH₃ F F H H A-605 CH₂CH₃ F F H H A-606 H F Cl H H A-607 F F Cl H H A-608 Cl F Cl H H A-609 CH₃ F Cl H H A-610 CH₂CH₃ F Cl H H A-611 H F CHF2 H H A-612 F F CHF2 H H A-613 Cl F CHF2 H H A-614 CH₃ F CHF2 H H A-615 CH₂CH₃ F CHF2 H H A-616 H F CF₃ H H A-617 F F CF₃ H H A-618 Cl F CF₃ H H A-619 CH₃ F CF₃ H H A-620 CH₂CH₃ F CF₃ H H A-621 H F SCHF₂ H H A-622 F F SCHF₂ H H A-623 Cl F SCHF₂ H H A-624 CH₃ F SCHF₂ H H A-625 CH₂CH₃ F SCHF₂ H H A-626 H F SCF₃ H H A-627 F F SCF₃ H H A-628 Cl F SCF₃ H H A-629 CH₃ F SCF₃ H H A-630 CH₂CH₃ F SCF₃ H H A-631 H F OCHF₂ H H A-632 F F OCHF₂ H H A-633 Cl F OCHF₂ H H A-634 CH₃ F OCHF₂ H H A-635 CH₂CH₃ F OCHF₂ H H A-636 H F OCF₃ H H A-637 F F OCF₃ H H A-638 Cl F OCF₃ H H A-639 CH₃ F OCF₃ H H A-640 CH₂CH₃ F OCF₃ H H A-641 H F F F H A-642 F F F F H A-643 Cl F F F H A-644 CH₃ F F F H A-645 CH₂CH₃ F F F H A-646 H F Cl F H A-647 F F Cl F H A-648 Cl F Cl F H A-649 CH₃ F Cl F H A-650 CH₂CH₃ F Cl F H A-651 H F CHF2 F H A-652 F F CHF2 F H A-653 Cl F CHF2 F H A-654 CH₃ F CHF2 F H A-655 CH₂CH₃ F CHF2 F H A-656 H F CF₃ F H A-657 F F CF₃ F H A-658 Cl F CF₃ F H A-659 CH₃ F CF₃ F H A-660 CH₂CH₃ F CF₃ F H A-661 H F SCHF₂ F H A-662 F F SCHF₂ F H A-663 Cl F SCHF₂ F H A-664 CH₃ F SCHF₂ F H A-665 CH₂CH₃ F SCHF₂ F H A-666 H F SCF₃ F H A-667 F F SCF₃ F H A-668 Cl F SCF₃ F H A-669 CH₃ F SCF₃ F H A-670 CH₂CH₃ F SCF₃ F H A-671 H F OCHF₂ F H A-672 F F OCHF₂ F H A-673 Cl F OCHF₂ F H A-674 CH₃ F OCHF₂ F H A-675 CH₂CH₃ F OCHF₂ F H A-676 H F OCF₃ F H A-677 F F OCF₃ F H A-678 Cl F OCF₃ F H A-679 CH₃ F OCF₃ F H A-680 CH₂CH₃ F OCF₃ F H A-681 H F F Cl H A-682 F F F Cl H A-683 Cl F F Cl H A-684 CH₃ F F Cl H A-685 CH₂CH₃ F F Cl H A-686 H F Cl Cl H A-687 F F Cl Cl H A-688 Cl F Cl Cl H A-689 CH₃ F Cl Cl H A-690 CH₂CH₃ F Cl Cl H A-691 H F CHF2 Cl H A-692 F F CHF2 Cl H A-693 Cl F CHF2 Cl H A-694 CH₃ F CHF2 Cl H A-695 CH₂CH₃ F CHF2 Cl H A-696 H F CF₃ Cl H A-697 F F CF₃ Cl H A-698 Cl F CF₃ Cl H A-699 CH₃ F CF₃ Cl H A-700 CH₂CH₃ F CF₃ Cl H A-701 H F SCHF₂ Cl H A-702 F F SCHF₂ Cl H A-703 Cl F SCHF₂ Cl H A-704 CH₃ F SCHF₂ Cl H A-705 CH₂CH₃ F SCHF₂ Cl H A-706 H F SCF₃ Cl H A-707 F F SCF₃ Cl H A-708 Cl F SCF₃ Cl H A-709 CH₃ F SCF₃ Cl H A-710 CH₂CH₃ F SCF₃ Cl H A-711 H F OCHF₂ Cl H A-712 F F OCHF₂ Cl H A-713 Cl F OCHF₂ Cl H A-714 CH₃ F OCHF₂ Cl H A-715 CH₂CH₃ F OCHF₂ Cl H A-716 H F OCF₃ Cl H A-717 F F OCF₃ Cl H A-718 Cl F OCF₃ Cl H A-719 CH₃ F OCF₃ Cl H A-720 CH₂CH₃ F OCF₃ Cl H A-721 H F F CHF₂ H A-722 F F F CHF₂ H A-723 Cl F F CHF₂ H A-724 CH₃ F F CHF₂ H A-725 CH₂CH₃ F F CHF₂ H A-726 H F Cl CHF₂ H A-727 F F Cl CHF₂ H A-728 Cl F Cl CHF₂ H A-729 CH₃ F Cl CHF₂ H A-730 CH₂CH₃ F Cl CHF₂ H A-731 H F CHF2 CHF₂ H A-732 F F CHF2 CHF₂ H A-733 Cl F CHF2 CHF₂ H A-734 CH₃ F CHF2 CHF₂ H A-735 CH₂CH₃ F CHF2 CHF₂ H A-736 H F CF₃ CHF₂ H A-737 F F CF₃ CHF₂ H A-738 Cl F CF₃ CHF₂ H A-739 CH₃ F CF₃ CHF₂ H A-740 CH₂CH₃ F CF₃ CHF₂ H A-741 H F SCHF₂ CHF₂ H A-742 F F SCHF₂ CHF₂ H A-743 Cl F SCHF₂ CHF₂ H A-744 CH₃ F SCHF₂ CHF₂ H A-745 CH₂CH₃ F SCHF₂ CHF₂ H A-746 H F SCF₃ CHF₂ H A-747 F F SCF₃ CHF₂ H A-748 Cl F SCF₃ CHF₂ H A-749 CH₃ F SCF₃ CHF₂ H A-750 CH₂CH₃ F SCF₃ CHF₂ H A-751 H F OCHF₂ CHF₂ H A-752 F F OCHF₂ CHF₂ H A-753 Cl F OCHF₂ CHF₂ H A-754 CH₃ F OCHF₂ CHF₂ H A-755 CH₂CH₃ F OCHF₂ CHF₂ H A-756 H F OCF₃ CHF₂ H A-757 F F OCF₃ CHF₂ H A-758 Cl F OCF₃ CHF₂ H A-759 CH₃ F OCF₃ CHF₂ H A-760 CH₂CH₃ F OCF₃ CHF₂ H A-761 H F F CF₃ H A-762 F F F CF₃ H A-763 Cl F F CF₃ H A-764 CH₃ F F CF₃ H A-765 CH₂CH₃ F F CF₃ H A-766 H F Cl CF₃ H A-767 F F Cl CF₃ H A-768 Cl F Cl CF₃ H A-769 CH₃ F Cl CF₃ H A-770 CH₂CH₃ F Cl CF₃ H A-771 H F CHF2 CF₃ H A-772 F F CHF2 CF₃ H A-773 Cl F CHF2 CF₃ H A-774 CH₃ F CHF2 CF₃ H A-775 CH₂CH₃ F CHF2 CF₃ H A-776 H F CF₃ CF₃ H A-777 F F CF₃ CF₃ H A-778 Cl F CF₃ CF₃ H A-779 CH₃ F CF₃ CF₃ H A-780 CH₂CH₃ F CF₃ CF₃ H A-781 H F SCHF₂ CF₃ H A-782 F F SCHF₂ CF₃ H A-783 Cl F SCHF₂ CF₃ H A-784 CH₃ F SCHF₂ CF₃ H A-785 CH₂CH₃ F SCHF₂ CF₃ H A-786 H F SCF₃ CF₃ H A-787 F F SCF₃ CF₃ H A-788 Cl F SCF₃ CF₃ H A-789 CH₃ F SCF₃ CF₃ H A-790 CH₂CH₃ F SCF₃ CF₃ H A-791 H F OCHF₂ CF₃ H A-792 F F OCHF₂ CF₃ H A-793 Cl F OCHF₂ CF₃ H A-794 CH₃ F OCHF₂ CF₃ H A-795 CH₂CH₃ F OCHF₂ CF₃ H A-796 H F OCF₃ CF₃ H A-797 F F OCF₃ CF₃ H A-798 Cl F OCF₃ CF₃ H A-799 CH₃ F OCF₃ CF₃ H A-800 CH₂CH₃ F OCF₃ CF₃ H A-801 H F F H F A-802 F F F H F A-803 Cl F F H F A-804 CH₃ F F H F A-805 CH₂CH₃ F F H F A-806 H F Cl H F A-807 F F Cl H F A-808 Cl F Cl H F A-809 CH₃ F Cl H F A-810 CH₂CH₃ F Cl H F A-811 H F CHF2 H F A-812 F F CHF2 H F A-813 Cl F CHF2 H F A-814 CH₃ F CHF2 H F A-815 CH₂CH₃ F CHF2 H F A-816 H F CF₃ H F A-817 F F CF₃ H F A-818 Cl F CF₃ H F A-819 CH₃ F CF₃ H F A-820 CH₂CH₃ F CF₃ H F A-821 H F SCHF₂ H F A-822 F F SCHF₂ H F A-823 Cl F SCHF₂ H F A-824 CH₃ F SCHF₂ H F A-825 CH₂CH₃ F SCHF₂ H F A-826 H F SCF₃ H F A-827 F F SCF₃ H F A-828 Cl F SCF₃ H F A-829 CH₃ F SCF₃ H F A-830 CH₂CH₃ F SCF₃ H F A-831 H F OCHF₂ H F A-832 F F OCHF₂ H F A-833 Cl F OCHF₂ H F A-834 CH₃ F OCHF₂ H F A-835 CH₂CH₃ F OCHF₂ H F A-836 H F OCF₃ H F A-837 F F OCF₃ H F A-838 Cl F OCF₃ H F A-839 CH₃ F OCF₃ H F A-840 CH₂CH₃ F OCF₃ H F A-841 H F F F F A-842 F F F F F A-843 Cl F F F F A-844 CH₃ F F F F A-845 CH₂CH₃ F F F F A-846 H F Cl F F A-847 F F Cl F F A-848 Cl F Cl F F A-849 CH₃ F Cl F F A-850 CH₂CH₃ F Cl F F A-851 H F CHF2 F F A-852 F F CHF2 F F A-853 Cl F CHF2 F F A-854 CH₃ F CHF2 F F A-855 CH₂CH₃ F CHF2 F F A-856 H F CF₃ F F A-857 F F CF₃ F F A-858 Cl F CF₃ F F A-859 CH₃ F CF₃ F F A-860 CH₂CH₃ F CF₃ F F A-861 H F SCHF₂ F F A-862 F F SCHF₂ F F A-863 Cl F SCHF₂ F F A-864 CH₃ F SCHF₂ F F A-865 CH₂CH₃ F SCHF₂ F F A-866 H F SCF₃ F F A-867 F F SCF₃ F F A-868 Cl F SCF₃ F F A-869 CH₃ F SCF₃ F F A-870 CH₂CH₃ F SCF₃ F F A-871 H F OCHF₂ F F A-872 F F OCHF₂ F F A-873 Cl F OCHF₂ F F A-874 CH₃ F OCHF₂ F F A-875 CH₂CH₃ F OCHF₂ F F A-876 H F OCF₃ F F A-877 F F OCF₃ F F A-878 Cl F OCF₃ F F A-879 CH₃ F OCF₃ F F A-880 CH₂CH₃ F OCF₃ F F A-881 H F F Cl F A-882 F F F Cl F A-883 Cl F F Cl F A-884 CH₃ F F Cl F A-885 CH₂CH₃ F F Cl F A-886 H F Cl Cl F A-887 F F Cl Cl F A-888 Cl F Cl Cl F A-889 CH₃ F Cl Cl F A-890 CH₂CH₃ F Cl Cl F A-891 H F CHF2 Cl F A-892 F F CHF2 Cl F A-893 Cl F CHF2 Cl F A-894 CH₃ F CHF2 Cl F A-895 CH₂CH₃ F CHF2 Cl F A-896 H F CF₃ Cl F A-897 F F CF₃ Cl F A-898 Cl F CF₃ Cl F A-899 CH₃ F CF₃ Cl F A-900 CH₂CH₃ F CF₃ Cl F A-901 H F SCHF₂ Cl F A-902 F F SCHF₂ Cl F A-903 Cl F SCHF₂ Cl F A-904 CH₃ F SCHF₂ Cl F A-905 CH₂CH₃ F SCHF₂ Cl F A-906 H F SCF₃ Cl F A-907 F F SCF₃ Cl F A-908 Cl F SCF₃ Cl F A-909 CH₃ F SCF₃ Cl F A-910 CH₂CH₃ F SCF₃ Cl F A-911 H F OCHF₂ Cl F A-912 F F OCHF₂ Cl F A-913 Cl F OCHF₂ Cl F A-914 CH₃ F OCHF₂ Cl F A-915 CH₂CH₃ F OCHF₂ Cl F A-916 H F OCF₃ Cl F A-917 F F OCF₃ Cl F A-918 Cl F OCF₃ Cl F A-919 CH₃ F OCF₃ Cl F A-920 CH₂CH₃ F OCF₃ Cl F A-921 H F F CHF₂ F A-922 F F F CHF₂ F A-923 Cl F F CHF₂ F A-924 CH₃ F F CHF₂ F A-925 CH₂CH₃ F F CHF₂ F A-926 H F Cl CHF₂ F A-927 F F Cl CHF₂ F A-928 Cl F Cl CHF₂ F A-929 CH₃ F Cl CHF₂ F A-930 CH₂CH₃ F Cl CHF₂ F A-931 H F CHF2 CHF₂ F A-932 F F CHF2 CHF₂ F A-933 Cl F CHF2 CHF₂ F A-934 CH₃ F CHF2 CHF₂ F A-935 CH₂CH₃ F CHF2 CHF₂ F A-936 H F CF₃ CHF₂ F A-937 F F CF₃ CHF₂ F A-938 Cl F CF₃ CHF₂ F A-939 CH₃ F CF₃ CHF₂ F A-940 CH₂CH₃ F CF₃ CHF₂ F A-941 H F SCHF₂ CHF₂ F A-942 F F SCHF₂ CHF₂ F A-943 Cl F SCHF₂ CHF₂ F A-944 CH₃ F SCHF₂ CHF₂ F A-945 CH₂CH₃ F SCHF₂ CHF₂ F A-946 H F SCF₃ CHF₂ F A-947 F F SCF₃ CHF₂ F A-948 Cl F SCF₃ CHF₂ F A-949 CH₃ F SCF₃ CHF₂ F A-950 CH₂CH₃ F SCF₃ CHF₂ F A-951 H F OCHF₂ CHF₂ F A-952 F F OCHF₂ CHF₂ F A-953 Cl F OCHF₂ CHF₂ F A-954 CH₃ F OCHF₂ CHF₂ F A-955 CH₂CH₃ F OCHF₂ CHF₂ F A-956 H F OCF₃ CHF₂ F A-957 F F OCF₃ CHF₂ F A-958 Cl F OCF₃ CHF₂ F A-959 CH₃ F OCF₃ CHF₂ F A-960 CH₂CH₃ F OCF₃ CHF₂ F A-961 H F F CF₃ F A-962 F F F CF₃ F A-963 Cl F F CF₃ F A-964 CH₃ F F CF₃ F A-965 CH₂CH₃ F F CF₃ F A-966 H F Cl CF₃ F A-967 F F Cl CF₃ F A-968 Cl F Cl CF₃ F A-969 CH₃ F Cl CF₃ F A-970 CH₂CH₃ F Cl CF₃ F A-971 H F CHF2 CF₃ F A-972 F F CHF2 CF₃ F A-973 Cl F CHF2 CF₃ F A-974 CH₃ F CHF2 CF₃ F A-975 CH₂CH₃ F CHF2 CF₃ F A-976 H F CF₃ CF₃ F A-977 F F CF₃ CF₃ F A-978 Cl F CF₃ CF₃ F A-979 CH₃ F CF₃ CF₃ F A-980 CH₂CH₃ F CF₃ CF₃ F A-981 H F SCHF₂ CF₃ F A-982 F F SCHF₂ CF₃ F A-983 Cl F SCHF₂ CF₃ F A-984 CH₃ F SCHF₂ CF₃ F A-985 CH₂CH₃ F SCHF₂ CF₃ F A-986 H F SCF₃ CF₃ F A-987 F F SCF₃ CF₃ F A-988 Cl F SCF₃ CF₃ F A-989 CH₃ F SCF₃ CF₃ F A-990 CH₂CH₃ F SCF₃ CF₃ F A-991 H F OCHF₂ CF₃ F A-992 F F OCHF₂ CF₃ F A-993 Cl F OCHF₂ CF₃ F A-994 CH₃ F OCHF₂ CF₃ F A-995 CH₂CH₃ F OCHF₂ CF₃ F A-996 H F OCF₃ CF₃ F A-997 F F OCF₃ CF₃ F A-998 Cl F OCF₃ CF₃ F A-999 CH₃ F OCF₃ CF₃ F A-1000 CH₂CH₃ F OCF₃ CF₃ F A-1001 H F F H Cl A-1002 F F F H Cl A-1003 Cl F F H Cl A-1004 CH₃ F F H Cl A-1005 CH₂CH₃ F F H Cl A-1006 H F Cl H Cl A-1007 F F Cl H Cl A-1008 Cl F Cl H Cl A-1009 CH₃ F Cl H Cl A-1010 CH₂CH₃ F Cl H Cl A-1011 H F CHF2 H Cl A-1012 F F CHF2 H Cl A-1013 Cl F CHF2 H Cl A-1014 CH₃ F CHF2 H Cl A-1015 CH₂CH₃ F CHF2 H Cl A-1016 H F CF₃ H Cl A-1017 F F CF₃ H Cl A-1018 Cl F CF₃ H Cl A-1019 CH₃ F CF₃ H Cl A-1020 CH₂CH₃ F CF₃ H Cl A-1021 H F SCHF₂ H Cl A-1022 F F SCHF₂ H Cl A-1023 Cl F SCHF₂ H Cl A-1024 CH₃ F SCHF₂ H Cl A-1025 CH₂CH₃ F SCHF₂ H Cl A-1026 H F SCF₃ H Cl A-1027 F F SCF₃ H Cl A-1028 Cl F SCF₃ H Cl A-1029 CH₃ F SCF₃ H Cl A-1030 CH₂CH₃ F SCF₃ H Cl A-1031 H F OCHF₂ H Cl A-1032 F F OCHF₂ H Cl A-1033 Cl F OCHF₂ H Cl A-1034 CH₃ F OCHF₂ H Cl A-1035 CH₂CH₃ F OCHF₂ H Cl A-1036 H F OCF₃ H Cl A-1037 F F OCF₃ H Cl A-1038 Cl F OCF₃ H Cl A-1039 CH₃ F OCF₃ H Cl A-1040 CH₂CH₃ F OCF₃ H Cl A-1041 H F F F Cl A-1042 F F F F Cl A-1043 Cl F F F Cl A-1044 CH₃ F F F Cl A-1045 CH₂CH₃ F F F Cl A-1046 H F Cl F Cl A-1047 F F Cl F Cl A-1048 Cl F Cl F Cl A-1049 CH₃ F Cl F Cl A-1050 CH₂CH₃ F Cl F Cl A-1051 H F CHF2 F Cl A-1052 F F CHF2 F Cl A-1053 Cl F CHF2 F Cl A-1054 CH₃ F CHF2 F Cl A-1055 CH₂CH₃ F CHF2 F Cl A-1056 H F CF₃ F Cl A-1057 F F CF₃ F Cl A-1058 Cl F CF₃ F Cl A-1059 CH₃ F CF₃ F Cl A-1060 CH₂CH₃ F CF₃ F Cl A-1061 H F SCHF₂ F Cl A-1062 F F SCHF₂ F Cl A-1063 Cl F SCHF₂ F Cl A-1064 CH₃ F SCHF₂ F Cl A-1065 CH₂CH₃ F SCHF₂ F Cl A-1066 H F SCF₃ F Cl A-1067 F F SCF₃ F Cl A-1068 Cl F SCF₃ F Cl A-1069 CH₃ F SCF₃ F Cl A-1070 CH₂CH₃ F SCF₃ F Cl A-1071 H F OCHF₂ F Cl A-1072 F F OCHF₂ F Cl A-1073 Cl F OCHF₂ F Cl A-1074 CH₃ F OCHF₂ F Cl A-1075 CH₂CH₃ F OCHF₂ F Cl A-1076 H F OCF₃ F Cl A-1077 F F OCF₃ F Cl A-1078 Cl F OCF₃ F Cl A-1079 CH₃ F OCF₃ F Cl A-1080 CH₂CH₃ F OCF₃ F Cl A-1081 H F F Cl Cl A-1082 F F F Cl Cl A-1083 Cl F F Cl Cl A-1084 CH₃ F F Cl Cl A-1085 CH₂CH₃ F F Cl Cl A-1086 H F Cl Cl Cl A-1087 F F Cl Cl Cl A-1088 Cl F Cl Cl Cl A-1089 CH₃ F Cl Cl Cl A-1090 CH₂CH₃ F Cl Cl Cl A-1091 H F CHF2 Cl Cl A-1092 F F CHF2 Cl Cl A-1093 Cl F CHF2 Cl Cl A-1094 CH₃ F CHF2 Cl Cl A-1095 CH₂CH₃ F CHF2 Cl Cl A-1096 H F CF₃ Cl Cl A-1097 F F CF₃ Cl Cl A-1098 Cl F CF₃ Cl Cl A-1099 CH₃ F CF₃ Cl Cl A-1100 CH₂CH₃ F CF₃ Cl Cl A-1101 H F SCHF₂ Cl Cl A-1102 F F SCHF₂ Cl Cl A-1103 Cl F SCHF₂ Cl Cl A-1104 CH₃ F SCHF₂ Cl Cl A-1105 CH₂CH₃ F SCHF₂ Cl Cl A-1106 H F SCF₃ Cl Cl A-1107 F F SCF₃ Cl Cl A-1108 Cl F SCF₃ Cl Cl A-1109 CH₃ F SCF₃ Cl Cl A-1110 CH₂CH₃ F SCF₃ Cl Cl A-1111 H F OCHF₂ Cl Cl A-1112 F F OCHF₂ Cl Cl A-1113 Cl F OCHF₂ Cl Cl A-1114 CH₃ F OCHF₂ Cl Cl A-1115 CH₂CH₃ F OCHF₂ Cl Cl A-1116 H F OCF₃ Cl Cl A-1117 F F OCF₃ Cl Cl A-1118 Cl F OCF₃ Cl Cl A-1119 CH₃ F OCF₃ Cl Cl A-1120 CH₂CH₃ F OCF₃ Cl Cl A-1121 H F F CHF₂ Cl A-1122 F F F CHF₂ Cl A-1123 Cl F F CHF₂ Cl A-1124 CH₃ F F CHF₂ Cl A-1125 CH₂CH₃ F F CHF₂ Cl A-1126 H F Cl CHF₂ Cl A-1127 F F Cl CHF₂ Cl A-1128 Cl F Cl CHF₂ Cl A-1129 CH₃ F Cl CHF₂ Cl A-1130 CH₂CH₃ F Cl CHF₂ Cl A-1131 H F CHF2 CHF₂ Cl A-1132 F F CHF2 CHF₂ Cl A-1133 Cl F CHF2 CHF₂ Cl A-1134 CH₃ F CHF2 CHF₂ Cl A-1135 CH₂CH₃ F CHF2 CHF₂ Cl A-1136 H F CF₃ CHF₂ Cl A-1137 F F CF₃ CHF₂ Cl A-1138 Cl F CF₃ CHF₂ Cl A-1139 CH₃ F CF₃ CHF₂ Cl A-1140 CH₂CH₃ F CF₃ CHF₂ Cl A-1141 H F SCHF₂ CHF₂ Cl A-1142 F F SCHF₂ CHF₂ Cl A-1143 Cl F SCHF₂ CHF₂ Cl A-1144 CH₃ F SCHF₂ CHF₂ Cl A-1145 CH₂CH₃ F SCHF₂ CHF₂ Cl A-1146 H F SCF₃ CHF₂ Cl A-1147 F F SCF₃ CHF₂ Cl A-1148 Cl F SCF₃ CHF₂ Cl A-1149 CH₃ F SCF₃ CHF₂ Cl A-1150 CH₂CH₃ F SCF₃ CHF₂ Cl A-1151 H F OCHF₂ CHF₂ Cl A-1152 F F OCHF₂ CHF₂ Cl A-1153 Cl F OCHF₂ CHF₂ Cl A-1154 CH₃ F OCHF₂ CHF₂ Cl A-1155 CH₂CH₃ F OCHF₂ CHF₂ Cl A-1156 H F OCF₃ CHF₂ Cl A-1157 F F OCF₃ CHF₂ Cl A-1158 Cl F OCF₃ CHF₂ Cl A-1159 CH₃ F OCF₃ CHF₂ Cl A-1160 CH₂CH₃ F OCF₃ CHF₂ Cl A-1161 H F F CF₃ Cl A-1162 F F F CF₃ Cl A-1163 Cl F F CF₃ Cl A-1164 CH₃ F F CF₃ Cl A-1165 CH₂CH₃ F F CF₃ Cl A-1166 H F Cl CF₃ Cl A-1167 F F Cl CF₃ Cl A-1168 Cl F Cl CF₃ Cl A-1169 CH₃ F Cl CF₃ Cl A-1170 CH₂CH₃ F Cl CF₃ Cl A-1171 H F CHF2 CF₃ Cl A-1172 F F CHF2 CF₃ Cl A-1173 Cl F CHF2 CF₃ Cl A-1174 CH₃ F CHF2 CF₃ Cl A-1175 CH₂CH₃ F CHF2 CF₃ Cl A-1176 H F CF₃ CF₃ Cl A-1177 F F CF₃ CF₃ Cl A-1178 Cl F CF₃ CF₃ Cl A-1179 CH₃ F CF₃ CF₃ Cl A-1180 CH₂CH₃ F CF₃ CF₃ Cl A-1181 H F SCHF₂ CF₃ Cl A-1182 F F SCHF₂ CF₃ Cl A-1183 Cl F SCHF₂ CF₃ Cl A-1184 CH₃ F SCHF₂ CF₃ Cl A-1185 CH₂CH₃ F SCHF₂ CF₃ Cl A-1186 H F SCF₃ CF₃ Cl A-1187 F F SCF₃ CF₃ Cl A-1188 Cl F SCF₃ CF₃ Cl A-1189 CH₃ F SCF₃ CF₃ Cl A-1190 CH₂CH₃ F SCF₃ CF₃ Cl A-1191 H F OCHF₂ CF₃ Cl A-1192 F F OCHF₂ CF₃ Cl A-1193 Cl F OCHF₂ CF₃ Cl A-1194 CH₃ F OCHF₂ CF₃ Cl A-1195 CH₂CH₃ F OCHF₂ CF₃ Cl A-1196 H F OCF₃ CF₃ Cl A-1197 F F OCF₃ CF₃ Cl A-1198 Cl F OCF₃ CF₃ Cl A-1199 CH₃ F OCF₃ CF₃ Cl A-1200 CH₂CH₃ F OCF₃ CF₃ Cl A-1201 H Cl F H H A-1202 F Cl F H H A-1203 Cl Cl F H H A-1204 CH₃ Cl F H H A-1205 CH₂CH₃ Cl F H H A-1206 H Cl Cl H H A-1207 F Cl Cl H H A-1208 Cl Cl Cl H H A-1209 CH₃ Cl Cl H H A-1210 CH₂CH₃ Cl Cl H H A-1211 H Cl CHF2 H H A-1212 F Cl CHF2 H H A-1213 Cl Cl CHF2 H H A-1214 CH₃ Cl CHF2 H H A-1215 CH₂CH₃ Cl CHF2 H H A-1216 H Cl CF₃ H H A-1217 F Cl CF₃ H H A-1218 Cl Cl CF₃ H H A-1219 CH₃ Cl CF₃ H H A-1220 CH₂CH₃ Cl CF₃ H H A-1221 H Cl SCHF₂ H H A-1222 F Cl SCHF₂ H H A-1223 Cl Cl SCHF₂ H H A-1224 CH₃ Cl SCHF₂ H H A-1225 CH₂CH₃ Cl SCHF₂ H H A-1226 H Cl SCF₃ H H A-1227 F Cl SCF₃ H H A-1228 Cl Cl SCF₃ H H A-1229 CH₃ Cl SCF₃ H H A-1230 CH₂CH₃ Cl SCF₃ H H A-1231 H Cl OCHF₂ H H A-1232 F Cl OCHF₂ H H A-1233 Cl Cl OCHF₂ H H A-1234 CH₃ Cl OCHF₂ H H A-1235 CH₂CH₃ Cl OCHF₂ H H A-1236 H Cl OCF₃ H H A-1237 F Cl OCF₃ H H A-1238 Cl Cl OCF₃ H H A-1239 CH₃ Cl OCF₃ H H A-1240 CH₂CH₃ Cl OCF₃ H H A-1241 H Cl F F H A-1242 F Cl F F H A-1243 Cl Cl F F H A-1244 CH₃ Cl F F H A-1245 CH₂CH₃ Cl F F H A-1246 H Cl Cl F H A-1247 F Cl Cl F H A-1248 Cl Cl Cl F H A-1249 CH₃ Cl Cl F H A-1250 CH₂CH₃ Cl Cl F H A-1251 H Cl CHF2 F H A-1252 F Cl CHF2 F H A-1253 Cl Cl CHF2 F H A-1254 CH₃ Cl CHF2 F H A-1255 CH₂CH₃ Cl CHF2 F H A-1256 H Cl CF₃ F H A-1257 F Cl CF₃ F H A-1258 Cl Cl CF₃ F H A-1259 CH₃ Cl CF₃ F H A-1260 CH₂CH₃ Cl CF₃ F H A-1261 H Cl SCHF₂ F H A-1262 F Cl SCHF₂ F H A-1263 Cl Cl SCHF₂ F H A-1264 CH₃ Cl SCHF₂ F H A-1265 CH₂CH₃ Cl SCHF₂ F H A-1266 H Cl SCF₃ F H A-1267 F Cl SCF₃ F H A-1268 Cl Cl SCF₃ F H A-1269 CH₃ Cl SCF₃ F H A-1270 CH₂CH₃ Cl SCF₃ F H A-1271 H Cl OCHF₂ F H A-1272 F Cl OCHF₂ F H A-1273 Cl Cl OCHF₂ F H A-1274 CH₃ Cl OCHF₂ F H A-1275 CH₂CH₃ Cl OCHF₂ F H A-1276 H Cl OCF₃ F H A-1277 F Cl OCF₃ F H A-1278 Cl Cl OCF₃ F H A-1279 CH₃ Cl OCF₃ F H A-1280 CH₂CH₃ Cl OCF₃ F H A-1281 H Cl F Cl H A-1282 F Cl F Cl H A-1283 Cl Cl F Cl H A-1284 CH₃ Cl F Cl H A-1285 CH₂CH₃ Cl F Cl H A-1286 H Cl Cl Cl H A-1287 F Cl Cl Cl H A-1288 Cl Cl Cl Cl H A-1289 CH₃ Cl Cl Cl H A-1290 CH₂CH₃ Cl Cl Cl H A-1291 H Cl CHF2 Cl H A-1292 F Cl CHF2 Cl H A-1293 Cl Cl CHF2 Cl H A-1294 CH₃ Cl CHF2 Cl H A-1295 CH₂CH₃ Cl CHF2 Cl H A-1296 H Cl CF₃ Cl H A-1297 F Cl CF₃ Cl H A-1298 Cl Cl CF₃ Cl H A-1299 CH₃ Cl CF₃ Cl H A-1300 CH₂CH₃ Cl CF₃ Cl H A-1301 H Cl SCHF₂ Cl H A-1302 F Cl SCHF₂ Cl H A-1303 Cl Cl SCHF₂ Cl H A-1304 CH₃ Cl SCHF₂ Cl H A-1305 CH₂CH₃ Cl SCHF₂ Cl H A-1306 H Cl SCF₃ Cl H A-1307 F Cl SCF₃ Cl H A-1308 Cl Cl SCF₃ Cl H A-1309 CH₃ Cl SCF₃ Cl H A-1310 CH₂CH₃ Cl SCF₃ Cl H A-1311 H Cl OCHF₂ Cl H A-1312 F Cl OCHF₂ Cl H A-1313 Cl Cl OCHF₂ Cl H A-1314 CH₃ Cl OCHF₂ Cl H A-1315 CH₂CH₃ Cl OCHF₂ Cl H A-1316 H Cl OCF₃ Cl H A-1317 F Cl OCF₃ Cl H A-1318 Cl Cl OCF₃ Cl H A-1319 CH₃ Cl OCF₃ Cl H A-1320 CH₂CH₃ Cl OCF₃ Cl H A-1321 H Cl F CHF₂ H A-1322 F Cl F CHF₂ H A-1323 Cl Cl F CHF₂ H A-1324 CH₃ F CHF₂ H A-1325 CH₂CH₃ Cl F CHF₂ H A-1326 H Cl Cl CHF₂ H A-1327 F Cl Cl CHF₂ H A-1328 Cl Cl Cl CHF₂ H A-1329 CH₃ Cl Cl CHF₂ H A-1330 CH₂CH₃ Cl Cl CHF₂ H A-1331 H Cl CHF2 CHF₂ H A-1332 F Cl CHF2 CHF₂ H A-1333 Cl Cl CHF2 CHF₂ H A-1334 CH₃ Cl CHF2 CHF₂ H A-1335 CH₂CH₃ Cl CHF2 CHF₂ H A-1336 H Cl CF₃ CHF₂ H A-1337 F Cl CF₃ CHF₂ H A-1338 Cl Cl CF₃ CHF₂ H A-1339 CH₃ Cl CF₃ CHF₂ H A-1340 CH₂CH₃ Cl CF₃ CHF₂ H A-1341 H Cl SCHF₂ CHF₂ H A-1342 F Cl SCHF₂ CHF₂ H A-1343 Cl Cl SCHF₂ CHF₂ H A-1344 CH₃ Cl SCHF₂ CHF₂ H A-1345 CH₂CH₃ Cl SCHF₂ CHF₂ H A-1346 H Cl SCF₃ CHF₂ H A-1347 F Cl SCF₃ CHF₂ H A-1348 Cl Cl SCF₃ CHF₂ H A-1349 CH₃ Cl SCF₃ CHF₂ H A-1350 CH₂CH₃ Cl SCF₃ CHF₂ H A-1351 H Cl OCHF₂ CHF₂ H A-1352 F Cl OCHF₂ CHF₂ H A-1353 Cl Cl OCHF₂ CHF₂ H A-1354 CH₃ Cl OCHF₂ CHF₂ H A-1355 CH₂CH₃ Cl OCHF₂ CHF₂ H A-1356 H Cl OCF₃ CHF₂ H A-1357 F Cl OCF₃ CHF₂ H A-1358 Cl Cl OCF₃ CHF₂ H A-1359 CH₃ Cl OCF₃ CHF₂ H A-1360 CH₂CH₃ Cl OCF₃ CHF₂ H A-1361 H Cl F CF₃ H A-1362 F Cl F CF₃ H A-1363 Cl Cl F CF₃ H A-1364 CH₃ Cl F CF₃ H A-1365 CH₂CH₃ Cl F CF₃ H A-1366 H Cl Cl CF₃ H A-1367 F Cl Cl CF₃ H A-1368 Cl Cl Cl CF₃ H A-1369 CH₃ Cl Cl CF₃ H A-1370 CH₂CH₃ Cl Cl CF₃ H A-1371 H Cl CHF2 CF₃ H A-1372 F Cl CHF2 CF₃ H A-1373 Cl Cl CHF2 CF₃ H A-1374 CH₃ Cl CHF2 CF₃ H A-1375 CH₂CH₃ Cl CHF2 CF₃ H A-1376 H Cl CF₃ CF₃ H A-1377 F Cl CF₃ CF₃ H A-1378 Cl Cl CF₃ CF₃ H A-1379 CH₃ Cl CF₃ CF₃ H A-1380 CH₂CH₃ Cl CF₃ CF₃ H A-1381 H Cl SCHF₂ CF₃ H A-1382 F Cl SCHF₂ CF₃ H A-1383 Cl Cl SCHF₂ CF₃ H A-1384 CH₃ Cl SCHF₂ CF₃ H A-1385 CH₂CH₃ Cl SCHF₂ CF₃ H A-1386 H Cl SCF₃ CF₃ H A-1387 F Cl SCF₃ CF₃ H A-1388 Cl Cl SCF₃ CF₃ H A-1389 CH₃ Cl SCF₃ CF₃ H A-1390 CH₂CH₃ Cl SCF₃ CF₃ H A-1391 H Cl OCHF₂ CF₃ H A-1392 F Cl OCHF₂ CF₃ H A-1393 Cl Cl OCHF₂ CF₃ H A-1394 CH₃ Cl OCHF₂ CF₃ H A-1395 CH₂CH₃ Cl OCHF₂ CF₃ H A-1396 H Cl OCF₃ CF₃ H A-1397 F Cl OCF₃ CF₃ H A-1398 Cl Cl OCF₃ CF₃ H A-1399 CH₃ Cl OCF₃ CF₃ H A-1400 CH₂CH₃ Cl OCF₃ CF₃ H A-1401 H Cl F H F A-1402 F F H F A-1403 Cl Cl F H F A-1404 CH₃ Cl F H F A-1405 CH₂CH₃ Cl F H F A-1406 H Cl Cl H F A-1407 F Cl Cl H F A-1408 Cl Cl Cl H F A-1409 CH₃ Cl Cl H F A-1410 CH₂CH₃ Cl Cl H F A-1411 H Cl CHF2 H F A-1412 F Cl CHF2 H F A-1413 Cl Cl CHF2 H F A-1414 CH₃ Cl CHF2 H F A-1415 CH₂CH₃ Cl CHF2 H F A-1416 H Cl CF₃ H F A-1417 F Cl CF₃ H F A-1418 Cl Cl CF₃ H F A-1419 CH₃ Cl CF₃ H F A-1420 CH₂CH₃ Cl CF₃ H F A-1421 H Cl SCHF₂ H F A-1422 F Cl SCHF₂ H F A-1423 Cl Cl SCHF₂ H F A-1424 CH₃ Cl SCHF₂ H F A-1425 CH₂CH₃ Cl SCHF₂ H F A-1426 H Cl SCF₃ H F A-1427 F Cl SCF₃ H F A-1428 Cl Cl SCF₃ H F A-1429 CH₃ Cl SCF₃ H F A-1430 CH₂CH₃ Cl SCF₃ H F A-1431 H Cl OCHF₂ H F A-1432 F Cl OCHF₂ H F A-1433 Cl Cl OCHF₂ H F A-1434 CH₃ Cl OCHF₂ H F A-1435 CH₂CH₃ Cl OCHF₂ H F A-1436 H Cl OCF₃ H F A-1437 F Cl OCF₃ H F A-1438 Cl Cl OCF₃ H F A-1439 CH₃ Cl OCF₃ H F A-1440 CH₂CH₃ Cl OCF₃ H F A-1441 H Cl F F F A-1442 F Cl F F F A-1443 Cl Cl F F F A-1444 CH₃ Cl F F F A-1445 CH₂CH₃ Cl F F F A-1446 H Cl Cl F F A-1447 F Cl Cl F F A-1448 Cl Cl Cl F F A-1449 CH₃ Cl Cl F F A-1450 CH₂CH₃ Cl Cl F F A-1451 H Cl CHF2 F F A-1452 F Cl CHF2 F F A-1453 Cl Cl CHF2 F F A-1454 CH₃ Cl CHF2 F F A-1455 CH₂CH₃ Cl CHF2 F F A-1456 H Cl CF₃ F F A-1457 F Cl CF₃ F F A-1458 Cl Cl CF₃ F F A-1459 CH₃ Cl CF₃ F F A-1460 CH₂CH₃ Cl CF₃ F F A-1461 H Cl SCHF₂ F F A-1462 F Cl SCHF₂ F F A-1463 Cl Cl SCHF₂ F F A-1464 CH₃ Cl SCHF₂ F F A-1465 CH₂CH₃ Cl SCHF₂ F F A-1466 H Cl SCF₃ F F A-1467 F Cl SCF₃ F F A-1468 Cl Cl SCF₃ F F A-1469 CH₃ Cl SCF₃ F F A-1470 CH₂CH₃ Cl SCF₃ F F A-1471 H Cl OCHF₂ F F A-1472 F Cl OCHF₂ F F A-1473 Cl Cl OCHF₂ F F A-1474 CH₃ Cl OCHF₂ F F A-1475 CH₂CH₃ Cl OCHF₂ F F A-1476 H Cl OCF₃ F F A-1477 F Cl OCF₃ F F A-1478 Cl Cl OCF₃ F F A-1479 CH₃ Cl OCF₃ F F A-1480 CH₂CH₃ Cl OCF₃ F F A-1481 H Cl F Cl F A-1482 F Cl F Cl F A-1483 Cl Cl F Cl F A-1484 CH₃ Cl F Cl F A-1485 CH₂CH₃ Cl F Cl F A-1486 H Cl Cl Cl F A-1487 F Cl Cl Cl F A-1488 Cl Cl Cl Cl F A-1489 CH₃ Cl Cl Cl F A-1490 CH₂CH₃ Cl Cl Cl F A-1491 H Cl CHF₂ Cl F A-1492 F Cl CHF₂ Cl F A-1493 Cl Cl CHF₂ Cl F A-1494 CH₃ Cl CHF₂ Cl F A-1495 CH₂CH₃ Cl CHF₂ Cl F A-1496 H Cl CF₃ Cl F A-1497 F Cl CF₃ Cl F A-1498 Cl Cl CF₃ Cl F A-1499 CH₃ Cl CF₃ Cl F A-1500 CH₂CH₃ Cl CF₃ Cl F A-1501 H Cl SCHF₂ Cl F A-1502 F Cl SCHF₂ Cl F A-1503 Cl Cl SCHF₂ Cl F A-1504 CH₃ Cl SCHF₂ Cl F A-1505 CH₂CH₃ Cl SCHF₂ Cl F A-1506 H Cl SCF₃ Cl F A-1507 F Cl SCF₃ Cl F A-1508 Cl Cl SCF₃ Cl F A-1509 CH₃ Cl SCF₃ Cl F A-1510 CH₂CH₃ Cl SCF₃ Cl F A-1511 H Cl OCHF₂ Cl F A-1512 F Cl OCHF₂ Cl F A-1513 Cl Cl OCHF₂ Cl F A-1514 CH₃ Cl OCHF₂ Cl F A-1515 CH₂CH₃ Cl OCHF₂ Cl F A-1516 H Cl OCF₃ Cl F A-1517 F Cl OCF₃ Cl F A-1518 Cl Cl OCF₃ Cl F A-1519 CH₃ Cl OCF₃ Cl F A-1520 CH₂CH₃ Cl OCF₃ Cl F A-1521 H Cl F CHF₂ F A-1522 F Cl F CHF₂ F A-1523 Cl Cl F CHF₂ F A-1524 CH₃ Cl F CHF₂ F A-1525 CH₂CH₃ Cl F CHF₂ F A-1526 H Cl Cl CHF₂ F A-1527 F Cl Cl CHF₂ F A-1528 Cl Cl Cl CHF₂ F A-1529 CH₃ Cl Cl CHF₂ F A-1530 CH₂CH₃ Cl Cl CHF₂ F A-1531 H Cl CHF₂ CHF₂ F A-1532 F Cl CHF₂ CHF₂ F A-1533 Cl Cl CHF₂ CHF₂ F A-1534 CH₃ Cl CHF₂ CHF₂ F A-1535 CH₂CH₃ Cl CHF₂ CHF₂ F A-1536 H Cl CF₃ CHF₂ F A-1537 F Cl CF₃ CHF₂ F A-1538 Cl Cl CF₃ CHF₂ F A-1539 CH₃ Cl CF₃ CHF₂ F A-1540 CH₂CH₃ Cl CF₃ CHF₂ F A-1541 H Cl SCHF₂ CHF₂ F A-1542 F Cl SCHF₂ CHF₂ F A-1543 Cl Cl SCHF₂ CHF₂ F A-1544 CH₃ Cl SCHF₂ CHF₂ F A-1545 CH₂CH₃ Cl SCHF₂ CHF₂ F A-1546 H Cl SCF₃ CHF₂ F A-1547 F Cl SCF₃ CHF₂ F A-1548 Cl Cl SCF₃ CHF₂ F A-1549 CH₃ Cl SCF₃ CHF₂ F A-1550 CH₂CH₃ Cl SCF₃ CHF₂ F A-1551 H Cl OCHF₂ CHF₂ F A-1552 F Cl OCHF₂ CHF₂ F A-1553 Cl Cl OCHF₂ CHF₂ F A-1554 CH₃ Cl OCHF₂ CHF₂ F A-1555 CH₂CH₃ Cl OCHF₂ CHF₂ F A-1556 H Cl OCF₃ CHF₂ F A-1557 F Cl OCF₃ CHF₂ F A-1558 Cl Cl OCF₃ CHF₂ F A-1559 CH₃ Cl OCF₃ CHF₂ F A-1560 CH₂CH₃ Cl OCF₃ CHF₂ F A-1561 H Cl F CF₃ F A-1562 F Cl F CF₃ F A-1563 Cl Cl F CF₃ F A-1564 CH₃ Cl F CF₃ F A-1565 CH₂CH₃ Cl F CF₃ F A-1566 H Cl Cl CF₃ F A-1567 F Cl Cl CF₃ F A-1568 Cl Cl Cl CF₃ F A-1569 CH₃ Cl Cl CF₃ F A-1570 CH₂CH₃ Cl Cl CF₃ F A-1571 H Cl CHF₂ CF₃ F A-1572 F Cl CHF₂ CF₃ F A-1573 Cl Cl CHF₂ CF₃ F A-1574 CH₃ Cl CHF₂ CF₃ F A-1575 CH₂CH₃ Cl CHF₂ CF₃ F A-1576 H Cl CF₃ CF₃ F A-1577 F Cl CF₃ CF₃ F A-1578 Cl Cl CF₃ CF₃ F A-1579 CH₃ Cl CF₃ CF₃ F A-1580 CH₂CH₃ Cl CF₃ CF₃ F A-1581 H Cl SCHF₂ CF₃ F A-1582 F Cl SCHF₂ CF₃ F A-1583 Cl Cl SCHF₂ CF₃ F A-1584 CH₃ Cl SCHF₂ CF₃ F A-1585 CH₂CH₃ Cl SCHF₂ CF₃ F A-1586 H Cl SCF₃ CF₃ F A-1587 F Cl SCF₃ CF₃ F A-1588 Cl Cl SCF₃ CF₃ F A-1589 CH₃ Cl SCF₃ CF₃ F A-1590 CH₂CH₃ Cl SCF₃ CF₃ F A-1591 H Cl OCHF₂ CF₃ F A-1592 F Cl OCHF₂ CF₃ F A-1593 Cl Cl OCHF₂ CF₃ F A-1594 CH₃ Cl OCHF₂ CF₃ F A-1595 CH₂CH₃ Cl OCHF₂ CF₃ F A-1596 H Cl OCF₃ CF₃ F A-1597 F Cl OCF₃ CF₃ F A-1598 Cl Cl OCF₃ CF₃ F A-1599 CH₃ Cl OCF₃ CF₃ F A-1600 CH₂CH₃ Cl OCF₃ CF₃ F A-1601 H Cl F H Cl A-1602 F Cl F H Cl A-1603 Cl Cl F H Cl A-1604 CH₃ Cl F H Cl A-1605 CH₂CH₃ Cl F H Cl A-1606 H Cl Cl H Cl A-1607 F Cl Cl H Cl A-1608 Cl Cl Cl H Cl A-1609 CH₃ Cl Cl H Cl A-1610 CH₂CH₃ Cl Cl H Cl A-1611 H Cl CHF₂ H Cl A-1612 F Cl CHF₂ H Cl A-1613 Cl Cl CHF₂ H Cl A-1614 CH₃ Cl CHF₂ H Cl A-1615 CH₂CH₃ Cl CHF₂ H Cl A-1616 H Cl CF₃ H Cl A-1617 F Cl CF₃ H Cl A-1618 Cl Cl CF₃ H Cl A-1619 CH₃ Cl CF₃ H Cl A-1620 CH₂CH₃ Cl CF₃ H Cl A-1621 H Cl SCHF₂ H Cl A-1622 F Cl SCHF₂ H Cl A-1623 Cl Cl SCHF₂ H Cl A-1624 CH₃ Cl SCHF₂ H Cl A-1625 CH₂CH₃ Cl SCHF₂ H Cl A-1626 H Cl SCF₃ H Cl A-1627 F Cl SCF₃ H Cl A-1628 Cl Cl SCF₃ H Cl A-1629 CH₃ Cl SCF₃ H Cl A-1630 CH₂CH₃ Cl SCF₃ H Cl A-1631 H Cl OCHF₂ H Cl A-1632 F Cl OCHF₂ H Cl A-1633 Cl Cl OCHF₂ H Cl A-1634 CH₃ Cl OCHF₂ H Cl A-1635 CH₂CH₃ Cl OCHF₂ H Cl A-1636 H Cl OCF₃ H Cl A-1637 F Cl OCF₃ H Cl A-1638 Cl Cl OCF₃ H Cl A-1639 CH₃ Cl OCF₃ H Cl A-1640 CH₂CH₃ Cl OCF₃ H Cl A-1641 H Cl F F Cl A-1642 F Cl F F Cl A-1643 Cl Cl F F Cl A-1644 CH₃ Cl F F Cl A-1645 CH₂CH₃ Cl F F Cl A-1646 H Cl Cl F Cl A-1647 F Cl Cl F Cl A-1648 Cl Cl Cl F Cl A-1649 CH₃ Cl Cl F Cl A-1650 CH₂CH₃ Cl Cl F Cl A-1651 H Cl CHF₂ F Cl A-1652 F Cl CHF₂ F Cl A-1653 Cl Cl CHF₂ F Cl A-1654 CH₃ Cl CHF₂ F Cl A-1655 CH₂CH₃ Cl CHF₂ F Cl A-1656 H Cl CF₃ F Cl A-1657 F Cl CF₃ F Cl A-1658 Cl Cl CF₃ F Cl A-1659 CH₃ Cl CF₃ F Cl A-1660 CH₂CH₃ Cl CF₃ F Cl A-1661 H Cl SCHF₂ F Cl A-1662 F Cl SCHF₂ F Cl A-1663 Cl Cl SCHF₂ F Cl A-1664 CH₃ Cl SCHF₂ F Cl A-1665 CH₂CH₃ Cl SCHF₂ F Cl A-1666 H Cl SCF₃ F Cl A-1667 F Cl SCF₃ F Cl A-1668 Cl Cl SCF₃ F Cl A-1669 CH₃ Cl SCF₃ F Cl A-1670 CH₂CH₃ Cl SCF₃ F Cl A-1671 H Cl OCHF₂ F Cl A-1672 F Cl OCHF₂ F Cl A-1673 Cl Cl OCHF₂ F Cl A-1674 CH₃ Cl OCHF₂ F Cl A-1675 CH₂CH₃ Cl OCHF₂ F Cl A-1676 H Cl OCF₃ F Cl A-1677 F Cl OCF₃ F Cl A-1678 Cl Cl OCF₃ F Cl A-1679 CH₃ Cl OCF₃ F Cl A-1680 CH₂CH₃ Cl OCF₃ F Cl A-1681 H Cl F Cl Cl A-1682 F Cl F Cl Cl A-1683 Cl Cl F Cl Cl A-1684 CH₃ Cl F Cl Cl A-1685 CH₂CH₃ Cl F Cl Cl A-1686 H Cl Cl Cl Cl A-1687 F Cl Cl Cl Cl A-1688 Cl Cl Cl Cl Cl A-1689 CH₃ Cl Cl Cl Cl A-1690 CH₂CH₃ Cl Cl Cl Cl A-1691 H Cl CHF₂ Cl Cl A-1692 F Cl CHF₂ Cl Cl A-1693 Cl Cl CHF₂ Cl Cl A-1694 CH₃ Cl CHF₂ Cl Cl A-1695 CH₂CH₃ Cl CHF₂ Cl Cl A-1696 H Cl CF₃ Cl Cl A-1697 F Cl CF₃ Cl Cl A-1698 Cl Cl CF₃ Cl Cl A-1699 CH₃ Cl CF₃ Cl Cl A-1700 CH₂CH₃ Cl CF₃ Cl Cl A-1701 H Cl SCHF₂ Cl Cl A-1702 F Cl SCHF₂ Cl Cl A-1703 Cl Cl SCHF₂ Cl Cl A-1704 CH₃ Cl SCHF₂ Cl Cl A-1705 CH₂CH₃ Cl SCHF₂ Cl Cl A-1706 H Cl SCF₃ Cl Cl A-1707 F Cl SCF₃ Cl Cl A-1708 Cl Cl SCF₃ Cl Cl A-1709 CH₃ Cl SCF₃ Cl Cl A-1710 CH₂CH₃ Cl SCF₃ Cl Cl A-1711 H Cl OCHF₂ Cl Cl A-1712 F Cl OCHF₂ Cl Cl A-1713 Cl Cl OCHF₂ Cl Cl A-1714 CH₃ Cl OCHF₂ Cl Cl A-1715 CH₂CH₃ Cl OCHF₂ Cl Cl A-1716 H Cl OCF₃ Cl Cl A-1717 F Cl OCF₃ Cl Cl A-1718 Cl Cl OCF₃ Cl Cl A-1719 CH₃ Cl OCF₃ Cl Cl A-1720 CH₂CH₃ Cl OCF₃ Cl Cl A-1721 H Cl F CHF₂ Cl A-1722 F Cl F CHF₂ Cl A-1723 Cl Cl F CHF₂ Cl A-1724 CH₃ Cl F CHF₂ Cl A-1725 CH₂CH₃ Cl F CHF₂ Cl A-1726 H Cl Cl CHF₂ Cl A-1727 F Cl Cl CHF₂ Cl A-1728 Cl Cl Cl CHF₂ Cl A-1729 CH₃ Cl Cl CHF₂ Cl A-1730 CH₂CH₃ Cl Cl CHF₂ Cl A-1731 H Cl CHF₂ CHF₂ Cl A-1732 F Cl CHF₂ CHF₂ Cl A-1733 Cl Cl CHF₂ CHF₂ Cl A-1734 CH₃ Cl CHF₂ CHF₂ Cl A-1735 CH₂CH₃ Cl CHF₂ CHF₂ Cl A-1736 H Cl CF₃ CHF₂ Cl A-1737 F Cl CF₃ CHF₂ Cl A-1738 Cl Cl CF₃ CHF₂ Cl A-1739 CH₃ Cl CF₃ CHF₂ Cl A-1740 CH₂CH₃ Cl CF₃ CHF₂ Cl A-1741 H Cl SCHF₂ CHF₂ Cl A-1742 F Cl SCHF₂ CHF₂ Cl A-1743 Cl Cl SCHF₂ CHF₂ Cl A-1744 CH₃ Cl SCHF₂ CHF₂ Cl A-1745 CH₂CH₃ Cl SCHF₂ CHF₂ Cl A-1746 H Cl SCF₃ CHF₂ Cl A-1747 F Cl SCF₃ CHF₂ Cl A-1748 Cl Cl SCF₃ CHF₂ Cl A-1749 CH₃ Cl SCF₃ CHF₂ Cl A-1750 CH₂CH₃ Cl SCF₃ CHF₂ Cl A-1751 H Cl OCHF₂ CHF₂ Cl A-1752 F Cl OCHF₂ CHF₂ Cl A-1753 Cl Cl OCHF₂ CHF₂ Cl A-1754 CH₃ Cl OCHF₂ CHF₂ Cl A-1755 CH₂CH₃ Cl OCHF₂ CHF₂ Cl A-1756 H Cl OCF₃ CHF₂ Cl A-1757 F Cl OCF₃ CHF₂ Cl A-1758 Cl Cl OCF₃ CHF₂ Cl A-1759 CH₃ Cl OCF₃ CHF₂ Cl A-1760 CH₂CH₃ Cl OCF₃ CHF₂ Cl A-1761 H Cl F CF₃ Cl A-1762 F Cl F CF₃ Cl A-1763 Cl Cl F CF₃ Cl A-1764 CH₃ Cl F CF₃ Cl A-1765 CH₂CH₃ Cl F CF₃ Cl A-1766 H Cl Cl CF₃ Cl A-1767 F Cl Cl CF₃ Cl A-1768 Cl Cl Cl CF₃ Cl A-1769 CH₃ Cl Cl CF₃ Cl A-1770 CH₂CH₃ Cl Cl CF₃ Cl A-1771 H Cl CHF₂ CF₃ Cl A-1772 F Cl CHF₂ CF₃ Cl A-1773 Cl Cl CHF₂ CF₃ Cl A-1774 CH₃ Cl CHF₂ CF₃ Cl A-1775 CH₂CH₃ Cl CHF₂ CF₃ Cl A-1776 H Cl CF₃ CF₃ Cl A-1777 F Cl CF₃ CF₃ Cl A-1778 Cl Cl CF₃ CF₃ Cl A-1779 CH₃ Cl CF₃ CF₃ Cl A-1780 CH₂CH₃ Cl CF₃ CF₃ Cl A-1781 H Cl SCHF₂ CF₃ Cl A-1782 F Cl SCHF₂ CF₃ Cl A-1783 Cl Cl SCHF₂ CF₃ Cl A-1784 CH₃ Cl SCHF₂ CF₃ Cl A-1785 CH₂CH₃ Cl SCHF₂ CF₃ Cl A-1786 H Cl SCF₃ CF₃ Cl A-1787 F Cl SCF₃ CF₃ Cl A-1788 Cl Cl SCF₃ CF₃ Cl A-1789 CH₃ Cl SCF₃ CF₃ Cl A-1790 CH₂CH₃ Cl SCF₃ CF₃ Cl A-1791 H Cl OCHF₂ CF₃ Cl A-1792 F Cl OCHF₂ CF₃ Cl A-1793 Cl Cl OCHF₂ CF₃ Cl A-1794 CH₃ Cl OCHF₂ CF₃ Cl A-1795 CH₂CH₃ Cl OCHF₂ CF₃ Cl A-1796 H Cl OCF₃ CF₃ Cl A-1797 F Cl OCF₃ CF₃ Cl A-1798 Cl Cl OCF₃ CF₃ Cl A-1799 CH₃ Cl OCF₃ CF₃ Cl A-1800 CH₂CH₃ Cl OCF₃ CF₃ Cl A-1801 H CH₃ F H H A-1802 F CH₃ F H H A-1803 Cl CH₃ F H H A-1804 CH₃ CH₃ F H H A-1805 CH₂CH₃ CH₃ F H H A-1806 H CH₃ Cl H H A-1807 F CH₃ Cl H H A-1808 Cl CH₃ Cl H H A-1809 CH₃ CH₃ Cl H H A-1810 CH₂CH₃ CH₃ Cl H H A-1811 H CH₃ CHF₂ H H A-1812 F CH₃ CHF₂ H H A-1813 Cl CH₃ CHF₂ H H A-1814 CH₃ CH₃ CHF₂ H H A-1815 CH₂CH₃ CH₃ CHF₂ H H A-1816 H CH₃ CF₃ H H A-1817 F CH₃ CF₃ H H A-1818 Cl CH₃ CF₃ H H A-1819 CH₃ CH₃ CF₃ H H A-1820 CH₂CH₃ CH₃ CF₃ H H A-1821 H CH₃ SCHF₂ H H A-1822 F CH₃ SCHF₂ H H A-1823 Cl CH₃ SCHF₂ H H A-1824 CH₃ CH₃ SCHF₂ H H A-1825 CH₂CH₃ CH₃ SCHF₂ H H A-1826 H CH₃ SCF₃ H H A-1827 F CH₃ SCF₃ H H A-1828 Cl CH₃ SCF₃ H H A-1829 CH₃ CH₃ SCF₃ H H A-1830 CH₂CH₃ CH₃ SCF₃ H H A-1831 H CH₃ OCHF₂ H H A-1832 F CH₃ OCHF₂ H H A-1833 Cl CH₃ OCHF₂ H H A-1834 CH₃ CH₃ OCHF₂ H H A-1835 CH₂CH₃ CH₃ OCHF₂ H H A-1836 H CH₃ OCF₃ H H A-1837 F CH₃ OCF₃ H H A-1838 Cl CH₃ OCF₃ H H A-1839 CH₃ CH₃ OCF₃ H H A-1840 CH₂CH₃ CH₃ OCF₃ H H A-1841 H CH₃ F F H A-1842 F CH₃ F F H A-1843 Cl CH₃ F F H A-1844 CH₃ CH₃ F F H A-1845 CH₂CH₃ CH₃ F F H A-1846 H CH₃ Cl F H A-1847 F CH₃ Cl F H A-1848 Cl CH₃ Cl F H A-1849 CH₃ CH₃ Cl F H A-1850 CH₂CH₃ CH₃ Cl F H A-1851 H CH₃ CHF₂ F H A-1852 F CH₃ CHF₂ F H A-1853 Cl CH₃ CHF₂ F H A-1854 CH₃ CH₃ CHF₂ F H A-1855 CH₂CH₃ CH₃ CHF₂ F H A-1856 H CH₃ CF₃ F H A-1857 F CH₃ CF₃ F H A-1858 Cl CH₃ CF₃ F H A-1859 CH₃ CH₃ CF₃ F H A-1860 CH₂CH₃ CH₃ CF₃ F H A-1861 H CH₃ SCHF₂ F H A-1862 F CH₃ SCHF₂ F H A-1863 Cl CH₃ SCHF₂ F H A-1864 CH₃ CH₃ SCHF₂ F H A-1865 CH₂CH₃ CH₃ SCHF₂ F H A-1866 H CH₃ SCF₃ F H A-1867 F CH₃ SCF₃ F H A-1868 Cl CH₃ SCF₃ F H A-1869 CH₃ CH₃ SCF₃ F H A-1870 CH₂CH₃ CH₃ SCF₃ F H A-1871 H CH₃ OCHF₂ F H A-1872 F CH₃ OCHF₂ F H A-1873 Cl CH₃ OCHF₂ F H A-1874 CH₃ CH₃ OCHF₂ F H A-1875 CH₂CH₃ CH₃ OCHF₂ F H A-1876 H CH₃ OCF₃ F H A-1877 F CH₃ OCF₃ F H A-1878 Cl CH₃ OCF₃ F H A-1879 CH₃ CH₃ OCF₃ F H A-1880 CH₂CH₃ CH₃ OCF₃ F H A-1881 H CH₃ F Cl H A-1882 F CH₃ F Cl H A-1883 Cl CH₃ F Cl H A-1884 CH₃ CH₃ F Cl H A-1885 CH₂CH₃ CH₃ F Cl H A-1886 H CH₃ Cl Cl H A-1887 F CH₃ Cl Cl H A-1888 Cl CH₃ Cl Cl H A-1889 CH₃ CH₃ Cl Cl H A-1890 CH₂CH₃ CH₃ Cl Cl H A-1891 H CH₃ CHF₂ Cl H A-1892 F CH₃ CHF₂ Cl H A-1893 Cl CH₃ CHF₂ Cl H A-1894 CH₃ CH₃ CHF₂ Cl H A-1895 CH₂CH₃ CH₃ CHF₂ Cl H A-1896 H CH₃ CF₃ Cl H A-1897 F CH₃ CF₃ Cl H A-1898 Cl CH₃ CF₃ Cl H A-1899 CH₃ CH₃ CF₃ Cl H A-1900 CH₂CH₃ CH₃ CF₃ Cl H A-1901 H CH₃ SCHF₂ Cl H A-1902 F CH₃ SCHF₂ Cl H A-1903 Cl CH₃ SCHF₂ Cl H A-1904 CH₃ CH₃ SCHF₂ Cl H A-1905 CH₂CH₃ CH₃ SCHF₂ Cl H A-1906 H CH₃ SCF₃ Cl H A-1907 F CH₃ SCF₃ Cl H A-1908 Cl CH₃ SCF₃ Cl H A-1909 CH₃ CH₃ SCF₃ Cl H A-1910 CH₂CH₃ CH₃ SCF₃ Cl H A-1911 H CH₃ OCHF₂ Cl H A-1912 F CH₃ OCHF₂ Cl H A-1913 Cl CH₃ OCHF₂ Cl H A-1914 CH₃ CH₃ OCHF₂ Cl H A-1915 CH₂CH₃ CH₃ OCHF₂ Cl H A-1916 H CH₃ OCF₃ Cl H A-1917 F CH₃ OCF₃ Cl H A-1918 Cl CH₃ OCF₃ Cl H A-1919 CH₃ CH₃ OCF₃ Cl H A-1920 CH₂CH₃ CH₃ OCF₃ Cl H A-1921 H CH₃ F CHF₂ H A-1922 F CH₃ F CHF₂ H A-1923 Cl CH₃ F CHF₂ H A-1924 CH₃ CH₃ F CHF₂ H A-1925 CH₂CH₃ CH₃ F CHF₂ H A-1926 H CH₃ Cl CHF₂ H A-1927 F CH₃ Cl CHF₂ H A-1928 Cl CH₃ Cl CHF₂ H A-1929 CH₃ CH₃ Cl CHF₂ H A-1930 CH₂CH₃ CH₃ Cl CHF₂ H A-1931 H CH₃ CHF₂ CHF₂ H A-1932 F CH₃ CHF₂ CHF₂ H A-1933 Cl CH₃ CHF₂ CHF₂ H A-1934 CH₃ CH₃ CHF₂ CHF₂ H A-1935 CH₂CH₃ CH₃ CHF₂ CHF₂ H A-1936 H CH₃ CF₃ CHF₂ H A-1937 F CH₃ CF₃ CHF₂ H A-1938 Cl CH₃ CF₃ CHF₂ H A-1939 CH₃ CH₃ CF₃ CHF₂ H A-1940 CH₂CH₃ CH₃ CF₃ CHF₂ H A-1941 H CH₃ SCHF₂ CHF₂ H A-1942 F CH₃ SCHF₂ CHF₂ H A-1943 Cl CH₃ SCHF₂ CHF₂ H A-1944 CH₃ CH₃ SCHF₂ CHF₂ H A-1945 CH₂CH₃ CH₃ SCHF₂ CHF₂ H A-1946 H CH₃ SCF₃ CHF₂ H A-1947 F CH₃ SCF₃ CHF₂ H A-1948 Cl CH₃ SCF₃ CHF₂ H A-1949 CH₃ CH₃ SCF₃ CHF₂ H A-1950 CH₂CH₃ CH₃ SCF₃ CHF₂ H A-1951 H CH₃ OCHF₂ CHF₂ H A-1952 F CH₃ OCHF₂ CHF₂ H A-1953 Cl CH₃ OCHF₂ CHF₂ H A-1954 CH₃ CH₃ OCHF₂ CHF₂ H A-1955 CH₂CH₃ CH₃ OCHF₂ CHF₂ H A-1956 H CH₃ OCF₃ CHF₂ H A-1957 F CH₃ OCF₃ CHF₂ H A-1958 Cl CH₃ OCF₃ CHF₂ H A-1959 CH₃ CH₃ OCF₃ CHF₂ H A-1960 CH₂CH₃ CH₃ OCF₃ CHF₂ H A-1961 H CH₃ F CF₃ H A-1962 F CH₃ F CF₃ H A-1963 Cl CH₃ F CF₃ H A-1964 CH₃ CH₃ F CF₃ H A-1965 CH₂CH₃ CH₃ F CF₃ H A-1966 H CH₃ Cl CF₃ H A-1967 F CH₃ Cl CF₃ H A-1968 Cl CH₃ Cl CF₃ H A-1969 CH₃ CH₃ Cl CF₃ H A-1970 CH₂CH₃ CH₃ Cl CF₃ H A-1971 H CH₃ CHF₂ CF₃ H A-1972 F CH₃ CHF₂ CF₃ H A-1973 Cl CH₃ CHF₂ CF₃ H A-1974 CH₃ CH₃ CHF₂ CF₃ H A-1975 CH₂CH₃ CH₃ CHF₂ CF₃ H A-1976 H CH₃ CF₃ CF₃ H A-1977 F CH₃ CF₃ CF₃ H A-1978 Cl CH₃ CF₃ CF₃ H A-1979 CH₃ CH₃ CF₃ CF₃ H A-1980 CH₂CH₃ CH₃ CF₃ CF₃ H A-1981 H CH₃ SCHF₂ CF₃ H A-1982 F CH₃ SCHF₂ CF₃ H A-1983 Cl CH₃ SCHF₂ CF₃ H A-1984 CH₃ CH₃ SCHF₂ CF₃ H A-1985 CH₂CH₃ CH₃ SCHF₂ CF₃ H A-1986 H CH₃ SCF₃ CF₃ H A-1987 F CH₃ SCF₃ CF₃ H A-1988 Cl CH₃ SCF₃ CF₃ H A-1989 CH₃ CH₃ SCF₃ CF₃ H A-1990 CH₂CH₃ CH₃ SCF₃ CF₃ H A-1991 H CH₃ OCHF₂ CF₃ H A-1992 F CH₃ OCHF₂ CF₃ H A-1993 Cl CH₃ OCHF₂ CF₃ H A-1994 CH₃ CH₃ OCHF₂ CF₃ H A-1995 CH₂CH₃ CH₃ OCHF₂ CF₃ H A-1996 H CH₃ OCF₃ CF₃ H A-1997 F CH₃ OCF₃ CF₃ H A-1998 Cl CH₃ OCF₃ CF₃ H A-1999 CH₃ CH₃ OCF₃ CF₃ H A-2000 CH₂CH₃ CH₃ OCF₃ CF₃ H A-2001 H CH₃ F H F A-2002 F CH₃ F H F A-2003 Cl CH₃ F H F A-2004 CH₃ CH₃ F H F A-2005 CH₂CH₃ CH₃ F H F A-2006 H CH₃ Cl H F A-2007 F CH₃ Cl H F A-2008 Cl CH₃ Cl H F A-2009 CH₃ CH₃ Cl H F A-2010 CH₂CH₃ CH₃ Cl H F A-2011 H CH₃ CHF₂ H F A-2012 F CH₃ CHF₂ H F A-2013 Cl CH₃ CHF₂ H F A-2014 CH₃ CH₃ CHF₂ H F A-2015 CH₂CH₃ CH₃ CHF₂ H F A-2016 H CH₃ CF₃ H F A-2017 F CH₃ CF₃ H F A-2018 Cl CH₃ CF₃ H F A-2019 CH₃ CH₃ CF₃ H F A-2020 CH₂CH₃ CH₃ CF₃ H F A-2021 H CH₃ SCHF₂ H F A-2022 F CH₃ SCHF₂ H F A-2023 Cl CH₃ SCHF₂ H F A-2024 CH₃ CH₃ SCHF₂ H F A-2025 CH₂CH₃ CH₃ SCHF₂ H F A-2026 H CH₃ SCF₃ H F A-2027 F CH₃ SCF₃ H F A-2028 Cl CH₃ SCF₃ H F A-2029 CH₃ CH₃ SCF₃ H F A-2030 CH₂CH₃ CH₃ SCF₃ H F A-2031 H CH₃ OCHF₂ H F A-2032 F CH₃ OCHF₂ H F A-2033 Cl CH₃ OCHF₂ H F A-2034 CH₃ CH₃ OCHF₂ H F A-2035 CH₂CH₃ CH₃ OCHF₂ H F A-2036 H CH₃ OCF₃ H F A-2037 F CH₃ OCF₃ H F A-2038 Cl CH₃ OCF₃ H F A-2039 CH₃ CH₃ OCF₃ H F A-2040 CH₂CH₃ CH₃ OCF₃ H F A-2041 H CH₃ F F F A-2042 F CH₃ F F F A-2043 Cl CH₃ F F F A-2044 CH₃ CH₃ F F F A-2045 CH₂CH₃ CH₃ F F F A-2046 H CH₃ Cl F F A-2047 F CH₃ Cl F F A-2048 Cl CH₃ Cl F F A-2049 CH₃ CH₃ Cl F F A-2050 CH₂CH₃ CH₃ Cl F F A-2051 H CH₃ CHF₂ F F A-2052 F CH₃ CHF₂ F F A-2053 Cl CH₃ CHF₂ F F A-2054 CH₃ CH₃ CHF₂ F F A-2055 CH₂CH₃ CH₃ CHF₂ F F A-2056 H CH₃ CF₃ F F A-2057 F CH₃ CF₃ F F A-2058 Cl CH₃ CF₃ F F A-2059 CH₃ CH₃ CF₃ F F A-2060 CH₂CH₃ CH₃ CF₃ F F A-2061 H CH₃ SCHF₂ F F A-2062 F CH₃ SCHF₂ F F A-2063 Cl CH₃ SCHF₂ F F A-2064 CH₃ CH₃ SCHF₂ F F A-2065 CH₂CH₃ CH₃ SCHF₂ F F A-2066 H CH₃ SCF₃ F F A-2067 F CH₃ SCF₃ F F A-2068 Cl CH₃ SCF₃ F F A-2069 CH₃ CH₃ SCF₃ F F A-2070 CH₂CH₃ CH₃ SCF₃ F F A-2071 H CH₃ OCHF₂ F F A-2072 F CH₃ OCHF₂ F F A-2073 Cl CH₃ OCHF₂ F F A-2074 CH₃ CH₃ OCHF₂ F F A-2075 CH₂CH₃ CH₃ OCHF₂ F F A-2076 H CH₃ OCF₃ F F A-2077 F CH₃ OCF₃ F F A-2078 Cl CH₃ OCF₃ F F A-2079 CH₃ CH₃ OCF₃ F F A-2080 CH₂CH₃ CH₃ OCF₃ F F A-2081 H CH₃ F Cl F A-2082 F CH₃ F Cl F A-2083 Cl CH₃ F Cl F A-2084 CH₃ CH₃ F Cl F A-2085 CH₂CH₃ CH₃ F Cl F A-2086 H CH₃ Cl Cl F A-2087 F CH₃ Cl Cl F A-2088 Cl CH₃ Cl Cl F A-2089 CH₃ CH₃ Cl Cl F A-2090 CH₂CH₃ CH₃ Cl Cl F A-2091 H CH₃ CHF₂ Cl F A-2092 F CH₃ CHF₂ Cl F A-2093 Cl CH₃ CHF₂ Cl F A-2094 CH₃ CH₃ CHF₂ Cl F A-2095 CH₂CH₃ CH₃ CHF₂ Cl F A-2096 H CH₃ CF₃ Cl F A-2097 F CH₃ CF₃ Cl F A-2098 Cl CH₃ CF₃ Cl F A-2099 CH₃ CH₃ CF₃ Cl F A-2100 CH₂CH₃ CH₃ CF₃ Cl F A-2101 H CH₃ SCHF₂ Cl F A-2102 F CH₃ SCHF₂ Cl F A-2103 Cl CH₃ SCHF₂ Cl F A-2104 CH₃ CH₃ SCHF₂ Cl F A-2105 CH₂CH₃ CH₃ SCHF₂ Cl F A-2106 H CH₃ SCF₃ Cl F A-2107 F CH₃ SCF₃ Cl F A-2108 Cl CH₃ SCF₃ Cl F A-2109 CH₃ CH₃ SCF₃ Cl F A-2110 CH₂CH₃ CH₃C SCF₃ Cl F A-2111 H CH₃C OCHF₂ Cl F A-2112 F CH₃ OCHF₂ Cl F A-2113 Cl CH₃ OCHF₂ Cl F A-2114 CH₃ CH₃C OCHF₂ Cl F A-2115 CH₂CH₃ CH₃C OCHF₂ Cl F A-2116 H CH₃ OCF₃ Cl F A-2117 F CH₃ OCF₃ Cl F A-2118 Cl CH₃ OCF₃ Cl F A-2119 CH₃ CH₃ OCF₃ Cl F A-2120 CH₂CH₃ CH₃ OCF₃ Cl F A-2121 H CH₃ F CHF₂ F A-2122 F CH₃ F CHF₂ F A-2123 Cl CH₃ F CHF₂ F A-2124 CH₃ CH₃ F CHF₂ F A-2125 CH₂CH₃ CH₃ F CHF₂ F A-2126 H CH₃ Cl CHF₂ F A-2127 F CH₃ Cl CHF₂ F A-2128 Cl CH₃ Cl CHF₂ F A-2129 CH₃ CH₃ Cl CHF₂ F A-2130 CH₂CH₃ CH₃ Cl CHF₂ F A-2131 H CH₃ CHF₂ CHF₂ F A-2132 F CH₃ CHF₂ CHF₂ F A-2133 Cl CH₃ CHF₂ CHF₂ F A-2134 CH₃ CH₃ CHF₂ CHF₂ F A-2135 CH₂CH₃ CH₃ CHF₂ CHF₂ F A-2136 H CH₃ CF₃ CHF₂ F A-2137 F CH₃ CF₃ CHF₂ F A-2138 Cl CH₃ CF₃ CHF₂ F A-2139 CH₃ CH₃ CF₃ CHF₂ F A-2140 CH₂CH₃ CH₃ CF₃ CHF₂ F A-2141 H CH₃ SCHF₂ CHF₂ F A-2142 F CH₃ SCHF₂ CHF₂ F A-2143 Cl CH₃ SCHF₂ CHF₂ F A-2144 CH₃ CH₃ SCHF₂ CHF₂ F A-2145 CH₂CH₃ CH₃ SCHF₂ CHF₂ F A-2146 H CH₃ SCF₃ CHF₂ F A-2147 F CH₃ SCF₃ CHF₂ F A-2148 Cl CH₃ SCF₃ CHF₂ F A-2149 CH₃ CH₃ SCF₃ CHF₂ F A-2150 CH₂CH₃ CH₃ SCF₃ CHF₂ F A-2151 H CH₃ OCHF₂ CHF₂ F A-2152 F CH₃ OCHF₂ CHF₂ F A-2153 Cl CH₃ OCHF₂ CHF₂ F A-2154 CH₃ CH₃ OCHF₂ CHF₂ F A-2155 CH₂CH₃ CH₃ OCHF₂ CHF₂ F A-2156 H CH₃ OCF₃ CHF₂ F A-2157 F CH₃ OCF₃ CHF₂ F A-2158 Cl CH₃ OCF₃ CHF₂ F A-2159 CH₃ CH₃ OCF₃ CHF₂ F A-2160 CH₂CH₃ CH₃ OCF₃ CHF₂ F A-2161 H CH₃ F CF₃ F A-2162 F CH₃ F CF₃ F A-2163 Cl CH₃ F CF₃ F A-2164 CH₃ CH₃ F CF₃ F A-2165 CH₂CH₃ CH₃ F CF₃ F A-2166 H CH₃ Cl CF₃ F A-2167 F CH₃ Cl CF₃ F A-2168 Cl CH₃ Cl CF₃ F A-2169 CH₃ CH₃ Cl CF₃ F A-2170 CH₂CH₃ CH₃ Cl CF₃ F A-2171 H CH₃ CHF₂ CF₃ F A-2172 F CH₃ CHF₂ CF₃ F A-2173 Cl CH₃ CHF₂ CF₃ F A-2174 CH₃ CH₃ CHF₂ CF₃ F A-2175 CH₂CH₃ CH₃ CHF₂ CF₃ F A-2176 H CH₃ CF₃ CF₃ F A-2177 F CH₃ CF₃ CF₃ F A-2178 Cl CH₃ CF₃ CF₃ F A-2179 CH₃ CH₃ CF₃ CF₃ F A-2180 CH₂CH₃ CH₃ CF₃ CF₃ F A-2181 H CH₃ SCHF₂ CF₃ F A-2182 F CH₃ SCHF₂ CF₃ F A-2183 Cl CH₃ SCHF₂ CF₃ F A-2184 CH₃ CH₃ SCHF₂ CF₃ F A-2185 CH₂CH₃ CH₃ SCHF₂ CF₃ F A-2186 H CH₃ SCF₃ CF₃ F A-2187 F CH₃ SCF₃ CF₃ F A-2188 Cl CH₃ SCF₃ CF₃ F A-2189 CH₃ CH₃ SCF₃ CF₃ F A-2190 CH₂CH₃ CH₃ SCF₃ CF₃ F A-2191 H CH₃ OCHF₂ CF₃ F A-2192 F CH₃ OCHF₂ CF₃ F A-2193 Cl CH₃ OCHF₂ CF₃ F A-2194 CH₃ CH₃ OCHF₂ CF₃ F A-2195 CH₂CH₃ CH₃ OCHF₂ CF₃ F A-2196 H CH₃ OCF₃ CF₃ F A-2197 F CH₃ OCF₃ CF₃ F A-2198 Cl CH₃ OCF₃ CF₃ F A-2199 CH₃ CH₃ OCF₃ CF₃ F A-2200 CH₂CH₃ CH₃ OCF₃ CF₃ F A-2201 H CH₃ F H Cl A-2202 F CH₃ F H Cl A-2203 Cl CH₃ F H Cl A-2204 CH₃ CH₃ F H Cl A-2205 CH₂CH₃ CH₃ F H Cl A-2206 H CH₃ Cl H Cl A-2207 F CH₃ Cl H Cl A-2208 Cl CH₃ Cl H Cl A-2209 CH₃ CH₃ Cl H Cl A-2210 CH₂CH₃ CH₃ Cl H Cl A-2211 H CH₃ CHF₂ H Cl A-2212 F CH₃ CHF₂ H Cl A-2213 Cl CH₃ CHF₂ H Cl A-2214 CH₃ CH₃ CHF₂ H Cl A-2215 CH₂CH₃ CH₃ CHF₂ H Cl A-2216 H CH₃ CF₃ H Cl A-2217 F CH₃ CF₃ H Cl A-2218 Cl CH₃ CF₃ H Cl A-2219 CH₃ CH₃ CF₃ H Cl A-2220 CH₂CH₃ CH₃ CF₃ H Cl A-2221 H CH₃ SCHF₂ H Cl A-2222 F CH₃ SCHF₂ H Cl A-2223 Cl CH₃ SCHF₂ H Cl A-2224 CH₃ CH₃ SCHF₂ H Cl A-2225 CH₂CH₃ CH₃ SCHF₂ H Cl A-2226 H CH₃ SCF₃ H Cl A-2227 F CH₃ SCF₃ H Cl A-2228 Cl CH₃ SCF₃ H Cl A-2229 CH₃ CH₃ SCF₃ H Cl A-2230 CH₂CH₃ CH₃ SCF₃ H Cl A-2231 H CH₃ OCHF₂ H Cl A-2232 F CH₃ OCHF₂ H Cl A-2233 Cl CH₃ OCHF₂ H Cl A-2234 CH₃ CH₃ OCHF₂ H Cl A-2235 CH₂CH₃ CH₃ OCHF₂ H Cl A-2236 H CH₃ OCF₃ H Cl A-2237 F CH₃ OCF₃ H Cl A-2238 Cl CH₃ OCF₃ H Cl A-2239 CH₃ CH₃ OCF₃ H Cl A-2240 CH₂CH₃ CH₃ OCF₃ H Cl A-2241 H CH₃ F F Cl A-2242 F CH₃ F F Cl A-2243 Cl CH₃ F F Cl A-2244 CH₃ CH₃ F F Cl A-2245 CH₂CH₃ CH₃ F F Cl A-2246 H CH₃ Cl F Cl A-2247 F CH₃ Cl F Cl A-2248 Cl CH₃ Cl F Cl A-2249 CH₃ CH₃ Cl F Cl A-2250 CH₂CH₃ CH₃ Cl F Cl A-2251 H CH₃ CHF₂ F Cl A-2252 F CH₃ CHF₂ F Cl A-2253 Cl CH₃ CHF₂ F Cl A-2254 CH₃ CH₃ CHF₂ F Cl A-2255 CH₂CH₃ CH₃ CHF₂ F Cl A-2256 H CH₃ CF₃ F Cl A-2257 F CH₃ CF₃ F Cl A-2258 Cl CH₃ CF₃ F Cl A-2259 CH₃ CH₃ CF₃ F Cl A-2260 CH₂CH₃ CH₃ CF₃ F Cl A-2261 H CH₃ SCHF₂ F Cl A-2262 F CH₃ SCHF₂ F Cl A-2263 Cl CH₃ SCHF₂ F Cl A-2264 CH₃ CH₃ SCHF₂ F Cl A-2265 CH₂CH₃ CH₃ SCHF₂ F Cl A-2266 H CH₃ SCF₃ F Cl A-2267 F CH₃ SCF₃ F Cl A-2268 Cl CH₃ SCF₃ F Cl A-2269 CH₃ CH₃ SCF₃ F Cl A-2270 CH₂CH₃ CH₃ SCF₃ F Cl A-2271 H CH₃ OCHF₂ F Cl A-2272 F CH₃ OCHF₂ F Cl A-2273 Cl CH₃ OCHF₂ F Cl A-2274 CH₃ CH₃ OCHF₂ F Cl A-2275 CH₂CH₃ CH₃ OCHF₂ F Cl A-2276 H CH₃ OCF₃ F Cl A-2277 F CH₃ OCF₃ F Cl A-2278 Cl CH₃ OCF₃ F Cl A-2279 CH₃ CH₃ OCF₃ F Cl A-2280 CH₂CH₃ CH₃ OCF₃ F Cl A-2281 H CH₃ F Cl Cl A-2282 F CH₃ F Cl Cl A-2283 Cl CH₃ F Cl Cl A-2284 CH₃ CH₃ F Cl Cl A-2285 CH₂CH₃ CH₃ F Cl Cl A-2286 H CH₃ Cl Cl Cl A-2287 F CH₃ Cl Cl Cl A-2288 Cl CH₃ Cl Cl Cl A-2289 CH₃ CH₃ Cl Cl Cl A-2290 CH₂CH₃ CH₃ Cl Cl Cl A-2291 H CH₃ CHF₂ Cl Cl A-2292 F CH₃ CHF₂ Cl Cl A-2293 Cl CH₃ CHF₂ Cl Cl A-2294 CH₃ CH₃ CHF₂ Cl Cl A-2295 CH₂CH₃ CH₃ CHF₂ Cl Cl A-2296 H CH₃ CF₃ Cl Cl A-2297 F CH₃ CF₃ Cl Cl A-2298 Cl CH₃ CF₃ Cl Cl A-2299 CH₃ CH₃ CF₃ Cl Cl A-2300 CH₂CH₃ CH₃ CF₃ Cl Cl A-2301 H CH₃ SCHF₂ Cl Cl A-2302 F CH₃ SCHF₂ Cl Cl A-2303 Cl CH₃ SCHF₂ Cl Cl A-2304 CH₃ CH₃ SCHF₂ Cl Cl A-2305 CH₂CH₃ CH₃ SCHF₂ Cl Cl A-2306 H CH₃ SCF₃ Cl Cl A-2307 F CH₃ SCF₃ Cl Cl A-2308 Cl CH₃ SCF₃ Cl Cl A-2309 CH₃ CH₃ SCF₃ Cl Cl A-2310 CH₂CH₃ CH₃ SCF₃ Cl Cl A-2311 H CH₃ OCHF₂ Cl Cl A-2312 F CH₃ OCHF₂ Cl Cl A-2313 Cl CH₃ OCHF₂ Cl Cl A-2314 CH₃ CH₃ OCHF₂ Cl Cl A-2315 CH₂CH₃ CH₃ OCHF₂ Cl Cl A-2316 H CH₃ OCF₃ Cl Cl A-2317 F CH₃ OCF₃ Cl Cl A-2318 Cl CH₃ OCF₃ Cl Cl A-2319 CH₃ CH₃ OCF₃ Cl Cl A-2320 CH₂CH₃ CH₃ OCF₃ Cl Cl A-2321 H CH₃ F CHF₂ Cl A-2322 F CH₃ F CHF₂ Cl A-2323 Cl CH₃ F CHF₂ Cl A-2324 CH₃ CH₃ F CHF₂ Cl A-2325 CH₂CH₃ CH₃ F CHF₂ Cl A-2326 H CH₃ Cl CHF₂ Cl A-2327 F CH₃ Cl CHF₂ Cl A-2328 Cl CH₃ Cl CHF₂ Cl A-2329 CH₃ CH₃ Cl CHF₂ Cl A-2330 CH₂CH₃ CH₃ Cl CHF₂ Cl A-2331 H CH₃ CHF₂ CHF₂ Cl A-2332 F CH₃ CHF₂ CHF₂ Cl A-2333 Cl CH₃ CHF₂ CHF₂ Cl A-2334 CH₃ CH₃ CHF₂ CHF₂ Cl A-2335 CH₂CH₃ CH₃ CHF₂ CHF₂ Cl A-2336 H CH₃ CF₃ CHF₂ Cl A-2337 F CH₃ CF₃ CHF₂ Cl A-2338 Cl CH₃ CF₃ CHF₂ Cl A-2339 CH₃ CH₃ CF₃ CHF₂ Cl A-2340 CH₂CH₃ CH₃ CF₃ CHF₂ Cl A-2341 H CH₃ SCHF₂ CHF₂ Cl A-2342 F CH₃ SCHF₂ CHF₂ Cl A-2343 Cl CH₃ SCHF₂ CHF₂ Cl A-2344 CH₃ CH₃ SCHF₂ CHF₂ Cl A-2345 CH₂CH₃ CH₃ SCHF₂ CHF₂ Cl A-2346 H CH₃ SCF₃ CHF₂ Cl A-2347 F CH₃ SCF₃ CHF₂ Cl A-2348 Cl CH₃ SCF₃ CHF₂ Cl A-2349 CH₃ CH₃ SCF₃ CHF₂ Cl A-2350 CH₂CH₃ CH₃ SCF₃ CHF₂ Cl A-2351 H CH₃ OCHF₂ CHF₂ Cl A-2352 F CH₃ OCHF₂ CHF₂ Cl A-2353 Cl CH₃ OCHF₂ CHF₂ Cl A-2354 CH₃ CH₃ OCHF₂ CHF₂ Cl A-2355 CH₂CH₃ CH₃ OCHF₂ CHF₂ Cl A-2356 H CH₃ OCF₃ CHF₂ Cl A-2357 F CH₃ OCF₃ CHF₂ Cl A-2358 Cl CH₃ OCF₃ CHF₂ Cl A-2359 CH₃ CH₃ OCF₃ CHF₂ Cl A-2360 CH₂CH₃ CH₃ OCF₃ CHF₂ Cl A-2361 H CH₃ F CF₃ Cl A-2362 F CH₃ F CF₃ Cl A-2363 Cl CH₃ F CF₃ Cl A-2364 CH₃ CH₃ F CF₃ Cl A-2365 CH₂CH₃ CH₃ F CF₃ Cl A-2366 H CH₃ Cl CF₃ Cl A-2367 F CH₃ Cl CF₃ Cl A-2368 Cl CH₃ Cl CF₃ Cl A-2369 CH₃ CH₃ Cl CF₃ Cl A-2370 CH₂CH₃ CH₃ Cl CF₃ Cl A-2371 H CH₃ CHF₂ CF₃ Cl A-2372 F CH₃ CHF₂ CF₃ Cl A-2373 Cl CH₃ CHF₂ CF₃ Cl A-2374 CH₃ CH₃ CHF₂ CF₃ Cl A-2375 CH₂CH₃ CH₃ CHF₂ CF₃ Cl A-2376 H CH₃ CF₃ CF₃ Cl A-2377 F CH₃ CF₃ CF₃ Cl A-2378 Cl CH₃ CF₃ CF₃ Cl A-2379 CH₃ CH₃ CF₃ CF₃ Cl A-2380 CH₂CH₃ CH₃ CF₃ CF₃ Cl A-2381 H CH₃ SCHF₂ CF₃ Cl A-2382 F CH₃ SCHF₂ CF₃ Cl A-2383 Cl CH₃ SCHF₂ CF₃ Cl A-2384 CH₃ CH₃ SCHF₂ CF₃ Cl A-2385 CH₂CH₃ CH₃ SCHF₂ CF₃ Cl A-2386 H CH₃ SCF₃ CF₃ Cl A-2387 F CH₃ SCF₃ CF₃ Cl A-2388 Cl CH₃ SCF₃ CF₃ Cl A-2389 CH₃ CH₃ SCF₃ CF₃ Cl A-2390 CH₂CH₃ CH₃ SCF₃ CF₃ Cl A-2391 H CH₃ OCHF₂ CF₃ Cl A-2392 F CH₃ OCHF₂ CF₃ Cl A-2393 Cl CH₃ OCHF₂ CF₃ Cl A-2394 CH₃ CH₃ OCHF₂ CF₃ Cl A-2395 CH₂CH₃ CH₃ OCHF₂ CF₃ Cl A-2396 H CH₃ OCF₃ CF₃ Cl A-2397 F CH₃ OCF₃ CF₃ Cl A-2398 Cl CH₃ OCF₃ CF₃ Cl A-2399 CH₃ CH₃ OCF₃ CF₃ Cl A-2400 CH₂CH₃ CH₃ OCF₃ CF₃ Cl

With respect to their use, very particular preference is given to the compounds I″ (R², R³, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹⁴ and R¹⁵ are hydrogen and R⁸ is methyl)

and in which

-   -   R¹ is hydrogen, fluorine or methyl;     -   R⁷ is hydrogen, methyl or ethyl;     -   R¹¹ is chlorine;     -   R¹² is trifluoromethyl;     -   R¹³ is hydrogen.

With respect to their use, very particular preference is also given to the compounds I′ in which

-   -   R¹ is hydrogen, fluorine or methyl;     -   R⁷ is hydrogen, methyl or ethyl;     -   R¹¹ is trifluoromethyl;     -   R¹² is hydrogen;     -   R¹³ is fluorine.

As mentioned at the outset, the S enantiomers or S diastereomers, with reference to the α carbon atom of the compounds listed in tables 1 to 96 are preferred.

The substituted phenylalanine derivatives of the formula I can be obtained by different routes, for example by solid-phase synthesis according to process 1 or 2:

Process 1:

A) Linking the Phenylalanine Derivative to a Carrier Resin

How to attach amino acid derivatives to a carrier resin is known and described, for example, in Barlos K. et al., Int J Pept Protein Res 37 (1991), 513; Barlos K. et al., Int J Pept Protein Res 47 (1991), 148; Barlos K. et al., Tetrahedron Lett. 30 (1989), 3943; Barlos K. et al., Tetrahedron Lett. 32 (1991), 471; Chhabra S. R. et al., Tetrahedron Lett. 39 (1998), 1603. A phenylalanine derivative II protected at the nitrogen function by a protective group X, for example by a 9-fluorenylmethoxycarbonyl (FMOC) protective group, a phenylmethoxycarbonyl (Cbz) group, a nitrobenzenelsulfenyl (Nps) group or a 1,1-dimethylethoxycarbonyl (Boc) group, is, in an esterification, attached to a resin which carries hydroxyl groups (see Scheme 1). The preparation of compounds II is known and is carried out analogously to known methods as described, for example, in Barlos K. et al., Int J Pept Protein Res 37 (1991), 513; Barlos K. et al., Int J Pept Protein Res 47 (1991), 148; Barlos K. et al., Tetrahedron Lett. 30 (1989), 3943; Barlos K. et al., Tetrahedron Lett. 32 (1991), 471; Chhabra S. R. et al., Tetrahedron Lett. 39 (1998), 1603. Furthermore, a large number of compounds II is commercially available. Here, the esterification is preferably carried out in the presence of a base, the ratio of base to compound II being approximately 2:1. Examples of suitable bases are amines, such as ethyldiisopropylamine, triethylamine or N-methylmorpholine. Suitable resins are for example resins based on polystyrene and having Wang or trityl linkers. The reaction is generally carried out in an inert organic solvent, for example an aromatic hydrocarbon such as benzene or toluene, or in a chlorinated hydrocarbon such as dichloromethane, or in an aprotic dipolar organic solvent such as dimethylformamide (DMF), dimethylacetamide (DMA) or N-methylpyrrolidone (NMP), or in an ether such as methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF). The reaction can be carried out at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature. B) Removal of the Protective Group X

In step B, the protective group X (see Scheme 2) is removed similarly to known methods, in the case of an FMOC protective group by adding a base such as, for example, piperidine or 1,5-diazabicyclo[4.3.0]non-5-ene in an aprotic dipolar organic solvent such as dimethylformamide (DMF), dimethylacetamide (DMA) or N-methylpyrrolidone (NMP) in a ratio of 1:1 to 1:5, giving compounds IV. The reaction can be carried out at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature.

C) N-Acylation

The N-acylation of step C can be carried out a) using a substituted benzoic acid V (process variant C.1) or b) using a benzoic acid derivative, for example a substituted benzoyl halide VI (process variant C.2), similarly to known processses, as described, for example, in Neustadt B. R. et al., Tetrahedron Lett. 39 (1998), 5317. C.1) N-Acylation Using a Substituted Benzoic Acid

Using compounds VI, compounds V can be converted into compounds III (see Scheme 3), for example by activating the carboxyl group of V with electrophilic reagents such as, for example, dicyclohexylcarbodiimide (DCC) or diisopropylcarbodiimide (DIC) in the presence of a catalytic amount of an organic base such as, for example, 4-dimethylaminopyridine or pyridine. If appropriate, further activation of the reaction can be achieved by using 1-hydroxybenzotriazole. The reaction is carried out until complete conversion is achieved, over a period of 4-12 h at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature, in an inert organic solvent such as, for example, an aromatic hydrocarbon, such as benzene or toluene, or in a chlorinated hydrocarbon, such as dichloromethane, or in organic solvents, such as dimethylformamide (DMF), dimethylacetamide (DMA) or N-methylpyrrolidone (NMP), methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF). The compounds V can be prepared similarly to known processes, as described, for example, in Houben-Weyl, “Methoden der organischen Chemie” [Methods of Organic Chemistry], 4^(th) edition, Ed. J. Talbe, New York 1985, pp. 193-585. Furthermore, a large number of compounds V is also commercially available. C.2) N-Acylation Using a Substituted Benzoyl Halide

To prepare compound VIII, compound IV can be reacted with a substituted benzoyl halide VI, by adding an organic base such as triethylamine, N-methylmorpholine or diisopropylethylamine (DIPEA) or else pyridine, if appropriate in the presence of a catalytic amount of 4-dimethylaminopyridine (see Scheme 4). The reaction takes place at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature, in an inert organic solvent, such as, for example, an aromatic hydrocarbon, such as benzene or toluene, or in a chlorinated hydrocarbon, such as dichloromethane, or in organic solvents such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF). The compounds VI can be prepared similarly to known methods, as described, for example, in Houben-Weyl, “Methoden der organischen Chemie”, 4^(th) edition, Ed. J. Talbe, pp. 587-615. Furthermore, a large number of the compounds VI is also 30 commercially available.

The derivatized amino acid attached to the resin is then cleaved from the resin using an acid, such as trifluoroacetic acid or acetic acid, in a polar solvent, such as 2,2,2-trifluoroethanol, dichloromethane or mixtures of the solvents mentioned above, if appropriate in the presence of water. It is possible to use, for example, mixtures of 2,2,2-trifluoroethanol/acetic acid/dichloromethane. D) Conversion of the N-Substituted Phenylalanine Derivative into Compound I

The conversion of the compound VIII into the phenylalanine derivatives of the formula I is carried out similarly to processes known from the literature, as described, for example, in Guan et al., J. Comb. Chem. 2 (2000), 297. Thus, the conversion of the derivatized amino acid into the amide I according to the invention can be carried out by adding an amine of the formula IX (see Scheme 5) in the presence of a resin-bound condensing agent, such as, for example, polystyrene-bound dicyclohexylcarbodiimide, at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature, in an inert aprotic dipolar organic solvent, such as dimethylformamide (DMF), dimethylacetamide (DMA) or N-methylpyrrolidone (NMP). Amines of the formula IX can be synthesized similarly to methods known to the person skilled in the art. Moreover, a large number of the amines IX is commercially available.

Process 2

Process 2 describes the preparation of compounds I in which R⁹=hydrogen. A Reductive Amination of a Polymer Resin X

The reductive amination of a polymer-bound aldehyde is carried out similarly to known methods as described, for example, in Fivush et al., Tetrahedron Lett. 38 (1997), 7151; del Fresno et al., Tetrahedron Lett. 39 (1998), 2639 and Bilodeau et al., J Org Chem. 63 (1998), 2800.

A suitable polymer resin, for example a 4-(4-formyl-3-methoxyphenoxy)butyrylaminomethylpolystyrene resin (Pol-CHO) X is, in the presence of a reducing agent, such as sodium cyanoborohydride or else sodium trisacetoxyborohydrid, if appropriate with addition of acetic acid, methanol or ethanol, reacted in an organic solvent, such as dimethylformamide (DMF), dimethylacetamide (DMA) or N-methylpyrrolidone (NMP), with an amine IX, giving an aminated resin XI (see Scheme 6). The reaction is carried out until complete conversion is achieved, for a period of 12-24 h, at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at 40-60° C. B N-Acylation Using a Substituted Phenylalanine Derivative

The compounds XI can be reacted with a phenylalanine derivative II which is protected at the nitrogen function by a protective group X, for example by a 9-fluorenylmethoxycarbonyl (FMOC) protective group, a phenylmethoxycarbonyl (Cbz) group, a nitrobenzenesulfenyl (Nps) group or a 1,1-dimethylethoxycarbonyl (Boc) group, to give the compounds XII. This can be achieved, for example, by activating the carboxyl group of II with electrophilic reagents, such as, for example, benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (PyBOP) or else with the aid of condensing agents, such as dicyclohexylcarbodiimide (DCC) or diisopropylcarbodiimide and addition of a catalytic amount of an organic base, such as, for example, N-methylmorpholine or 4-dimethylaminopyridine. The reaction is carried out until complete conversion is achieved, for a period of 12-24 h, at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature, in an inert organic solvent, such as, for example, an aromatic hydrocarbon, such as benzene or toluene, or in a chlorinated hydrocarbon, such as dichloromethane, or in organic solvents, such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF).

C) Removal of the Protective Group X

The protective group X is removed analogously to step B of process 1, giving compounds XIII

D) N-Acylation

The subsequent N-acylation to give the compounds I can be carried out similarly to the procedure described in step C.1 or C.2 of process 1, using a) a substituted benzoic acid V or [lacuna] a benzoic acid derivative, for example a substituted benzoyl halide VI, giving the compounds XIV

The derivatized amino acid which is attached to the resin is then cleaved from the resin using an acid, such as trifluoroacetic acid or acetic acid, in a polar solvent, such as 2,2,2-trifluoroethanol, dichloromethane or mixtures of the solvents mentioned above, if appropriate in the presence of water. It is possible, for example, to use mixtures of 2,2,2-trifluoroethanol/acetic acid/dichloromethane, giving the compounds I in which R⁹=hydrogen.

It is furthermore possible to prepare compounds I in liquid phase.

Process 3

A) Amination

Here, a phenylalanine derivative II protected at the nitrogen function by a protective group X, for example by a 9-fluorenylmethoxycarbonyl (FMOC) protective group, a phenylmethoxycarbonyl (Cbz) group, a nitrobenzenesulfenyl (Nps) group or a 1,1-dimethylethoxycarbonyl (Boc) group, is initially reacted with an amine IX in the presence of a suitable condensing agent, such as, for example, dicyclohexylcarbodiimide or diisopropylcarbodiimide, to give the compounds XV

If appropriate, further activation of the reaction can be achieved by using 1-hydroxybenzotriazole. The reaction is carried out until complete conversion has been achieved, over a period of 4-12 h, at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at room temperature, in an inert organic solvent, such as, for example, an aromatic hydrocarbon, such as benzene or toluene, or in a chlorinated hydrocarbon, such as dichloromethane, or in organic solvents, such as dimethylformamide (DMF), methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF). The reaction is carried out similarly to known methods as described, for example, in Bouygues et al., Med. Chem. 33 (1998) 445-450.

B) Removal of the Protective Group X

Depending on the protective group used, the protective group X is removed under basic, acidic or reductive conditions, for the Fmoc protective group, for example, analogously to step B of process 1, giving compounds XVI

C) N-Acylation

The subsequent N-acylation to give the compounds I can be carried out similarly to the procedure described in step C.1 or C.2 of process 1, using a) a substituted benzoic acid V or [lacuna] a benzoic acid derivative, for example a substituted benzoyl halide VI.

Process 4

Substituted phenylalanine derivatives I in which R¹⁰=hydrogen can also be prepared analogously to the “malonic ester synthesis” using an aminomalonic acid ester such as diethyl aminomalonate.

Step A)

Here, the salt (for example the chloride) of an ammoniummalonic acid ester

in which R¹ is a low-molecular-weight organic radical, for example a C₁-C₄-alkyl radical, preferably an easily obtainable, cheap compound, such as, for example, diethyl aminomalonate or dimethyl aminomalonate is initially reacted with a substituted benzoic acid, for example a substituted benzoyl halide VI, in the presence of a base, such as ethyldiisopropylamine, triethylamine or N-methylmorpholine, giving compounds XVII

The reaction is carried out until complete conversion has been achieved, for a period of 4-12 h, at temperatures of from −15° C. to the boiling point of the reaction mixture, preferably at 0° C., in an inert organic solvent, such as, for example, an aromatic hydrocarbon, such as benzene or toluene, or in a chlorinated hydrocarbon, such as dichloromethane, or in organic solvents, such as dimethylformamide (DMF), methyl t-butyl ether, diethyl ether or tetrahydrofuran (THF).

Step B)

The product obtained in step A) is reacted with a benzyl derivative XVIII

carrying a leaving group z, in an organic solvent, such as, for example, a cyclic ether, such as tetrahydrofuran (THF) or dioxane, in the presence of a base such as potassium tert-butoxide, sodium ethoxide, potassium carbonate or sodium carbonate, to give the diesters XIX

Suitable leaving groups z are, for example, halide or organosulfonyl groups. The reaction is carried out until complete conversion has been achieved, for a period of 4-12 h, at temperatures of from 0° C. to the boiling point of the reaction mixture, preferably at 80° C.

Step C)

Decarboxylation and hydrolysis of the diester XIX to give the compounds XX

are carried out in the presence of a base and water, for example aqueous sodium hydroxide solution or aqueous potassium hydroxide solution, in one of the organic solvents mentioned in step B. The mixture is subsequently neutralized to a pH below 7, preferably a pH of 1-2, using a strong mineral acid, such as, for example, hydrochloric acid. Step D)

The reaction of the acid of XX with an amine IX in the presence of resin-bound dicyclohexylcarbodiimide (DCC) is carried out analogously to the reaction conditions described in process 1, step D.

Process 5

Alternatively, the compounds of the formula 1 according to the invention can also be obtained by reacting the benzyl derivative XVIII with an alkylating agent XXI to give the compounds XXII. The methods for this purpose are known to the person skilled in the art (see, for example, 0 Donnell et al., Aldrichimica Acta Vol. 34 No. 1, 2001, pages 3 to 15) known.

The further conversion into XXIII can be carried out analogously to the methods described in process 1, step C.1 or step C.2 by reacting the compound XXII with the benzyl derivative V or VI to give compound XXIII.

Subsequent conversion of XXIII into the compounds I can be effected using amine IX. Methods for this purpose can be found, for example, in DE 3917880 or J. het. Chem. 1991, 28, 33 ff.

The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds I or the herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The application should also include the use as growth regulator. The customary “WR” part was introduced here. If this does not cover the effects observed or if amendments are desired, please get back to me.

Furthermore, the compounds of the formula I are also suitable for regulating the growth of plants of plants.

The compounds I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure a very fine distribution of the active compounds according to the invention.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the phenylalanine derivatives, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably from 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

-   -   I. 20 parts by weight of the compound No. I-19 are dissolved in         a mixture consisting of 80 parts by weight of alkylated benzene,         10 parts by weight of the adduct of 8 to 10 mol of ethylene         oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by         weight of calcium dodecylbenzenesulfonate and 5 parts by weight         of the adduct of 40 mol of ethylene oxide to 1 mol of castor         oil. Pouring the solution into 100,000 parts by weight of water         and finely distributing it therein gives an aqueous dispersion         which comprises 0.02% by weight of the active compound.     -   II. 20 parts by weight of the compound No. I-24 are dissolved in         a mixture consisting of 40 parts by weight of cyclohexanone, 30         parts by weight of isobutanol, 20 parts by weight of the adduct         of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10         parts by weight of the adduct of 40 mol of ethylene oxide to 1         mol of castor oil. Pouring the solution into 100,000 parts by         weight of water and finely distributing it therein gives an         aqueous dispersion which comprises 0.02% by weight of the active         compound.     -   III. 20 parts by weight of the active compound No. I-25 are         dissolved in a mixture consisting of 25 parts by weight of         cyclohexanone, 65 parts by weight of a mineral oil fraction of         boiling point 210 to 280° C. and 10 parts by weight of the         adduct of 40 mol of ethylene oxide to 1 mol of castor oil.         Pouring the solution into 100,000 parts by weight of water and         finely distributing it therein gives an aqueous dispersion which         comprises 0.02% by weight of the active compound.     -   IV. 20 parts by weight of the active compound No. I-32 are mixed         thoroughly with 3 parts by weight of sodium         diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium         salt of a lignosulfonic acid from a sulfite waste liquor and 60         parts by weight of pulverulent silica gel, and the mixture is         ground in a hammer mill. Finely distributing the mixture in         20,000 parts by weight of water gives a spray mixture which         comprises 0.1% by weight of the active compound.     -   V. 3 parts by weight of the active compound No. I-49 are mixed         with 97 parts by weight of finely divided kaolin. This gives a         dust which comprises 3% by weight of the active compound.     -   VI. 20 parts by weight of the active compound No. I-44 are mixed         intimately with 2 parts by weight of the calcium salt of         dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol         polyglycol ether, 2 parts by weight of the sodium salt of a         phenol/urea/formaldehyde condensate and 68 parts by weight of a         paraffinic mineral oil. This gives a stable oily dispersion.     -   VII. 1 part by weight of the compound No. I-26 is dissolved in a         mixture consisting of 70 parts by weight of cyclohexanone, 20         parts by weight of ethoxylated isooctylphenol and 10 parts by         weight of ethoxylated castor oil. This gives a stable emulsion         concentrate.     -   VIII. 1 part by weight of the compound No. I-3 is dissolved in a         mixture consisting of 80 parts by weight of cyclohexanone and 20         parts by weight of Wettol® EM 31 (nonionic emulsifier based on         ethoxylated castor oil). This gives a stable emulsion         concentrate.

The active compounds I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The growth-regulating compositions can be applied by the pre-emergence method or by the post-emergence method.

Depending on the season, the control target, the target plants and the growth stage, the application rates of the growth-regulating compositions of the formula I are, when used to regulate growth, from 0.001 to 5.0, preferably from 0.01 to 1.0, kg of active substance (a.s.)/ha:

The compounds of the formula I are capable of influencing virtually all development stages of a plant in various ways and are therefore used as growth regulators. The wide range of activity of the plant growth regualtors depends in particular

-   -   a) on the plant species and variety;     -   b) on the time of application, based on the stage of development         of the plant, and on the season;     -   c) on the site of application and method of application, for         example (seed dressing, soil treatment, foliage application or         trunk injection in the case of trees     -   d) on climatic factors, for example temperature, amount of         precipitation and also length of day and intensity of light;     -   e) on the soil characteristics (including fertilizer         application),     -   f) on the formulation or application form of the         growth-regulating composition of the formula I and finally     -   g) on the concentrations in which the active substance is used.

Of the number of different possible methods of application of the compound I as growth regulator in plant cultivation, in agriculture and in horticulture, some are stated below.

A. The compounds which can be used according to the invention permit considerable inhibition of the vegetative growth of the plants, which is evident in particular from a reduction in the growth in length. Accordingly, the treated plants exhibit stunted growth; in addition, a dark leaf coloration is observed. Reduced intensity of the growth of grasses at the edges of roads, in hedges, on canal embankments and on lawn areas such as parks, sports facilities, orchards, ornamental lawns and airfields, proves advantageous in practice, making it possible to reduce the labor-intensive and expensive cutting of grass.

The increase in the stability of crops susceptible to lodging, such as cereals, corn, sunflowers and soybean, is also of economic interest. The resulting shortening and strengthening of the stem reduce or eliminate the danger of lodging (bending) of plants under unfavorable weather conditions prior to harvesting.

The use of growth regulators for inhibiting the growth in length and for changing the time of ripening of cotton is also important. This permits completely mechanized harvesting of this important crop.

In the case of fruit trees and other trees, the growth regulators can be used to save pruning costs. In addition, the alternate bearing of fruit trees can be broken by means of growth regulators.

By using growth regulators, it is also possible to increase or inhibit the lateral branching of the plants. This is of interest when, for example in the case of tobacco plants, it is intended to inhibit the formation of side shoots in favor of leaf growth.

Growth regulators can also be used to effect a considerable increase in frost resistance, for example in the case of winter rape. On the one hand, the growth in length and the development to form a leaf or plant mass which is excessively luxuriant (and therefore particularly susceptible to frost) are inhibited. On the other hand, the young rape plants are held back in the vegetative stage of development after sowing and prior to the onset of the winter frosts, in spite of favorable growth conditions. This also eliminates the danger of frost damage to plants which tend toward a premature decline in the inhibition of blooming and toward a transition into the generative phase. In other crops too, for example winter cereals, it is advantageous if the crops are well tillered as a result of treatment with novel compounds in the fall but do not begin the winter with excessively luxuriant foliage. Increased sensitivity to frost and, owing to the relatively small leaf or plant mass, attack by various diseases (for example fungal disease) can thus be prevented. In addition, the inhibition of vegetative growth permits denser planting of the soil in the case of many crops, so that it is possible to achieve a higher yield, based on the soil area.

B. With the compounds of the formula I, it is possible to achieve higher yields of both plant parts and plant ingredients. Thus, it is possible, for example, to induce the growth of larger amounts of buds, blooms, leaves, fruits, seeds, roots and tubers, to increase the content of sugar in sugar beets, sugar cane and citrus fruits, to increase the protein content of cereals or soybean or to stimulate greater latex flow in rubber trees. The compounds of the formula I can produce increases in the yield by intervening in the metabolism of the plant or by promoting or inhibiting the vegetative and/or generative growth.

C. Finally, plant growth regulators can be used both for shortening or lengthening the stages of development and for accelerating or slowing down the ripening of the plant parts to be harvested prior to the harvest or of the harvested plant parts after harvesting.

For example, facilitating harvesting is of commercial interest and is permitted by concentrated dropping of fruit or a reduction of the strength of attachment to the tree in the case of citrus fruits, olives or other species and varieties of pomes, drupes and shell fruit. The same mechanism, ie. the promotion of the formation of abscission tissue between fruit part or leaf part and shoot part of the plant is also essential for readily controllable defoliation of useful plants, for example cotton.

D. Furthermore, the compounds of the formula I can be used to reduce the water consumption of plants. This is particularly important for agriculturally useful areas which have to be irrigated at high cost, for example in arid or semiarid regions. By using the novel substances, it is possible to reduce the intensity of irrigation and hence to carry out more economical farming. Under the influence of the compounds of the formula I, better utilization of the available water is achieved because, inter alia,

-   -   the extent of opening of the stomata is reduced     -   a thicker epidermis and cuticle are formed     -   the root penetration of the soil is improved and     -   the microclimate in the crop is advantageously influenced by         more compact growth.

The compounds of the formula I which are to be used according to the invention as growth regulators can be fed to the crops both via the seed (as seed dressing) and via the soil, i.e. through the roots and, particularly preferably, via the foliage by spraying.

To widen the activity spectrum and to achieve synergistic effects, the phenylalanine derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxy-alkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(aroyl/hetaroyl)-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitro-anilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyl-uracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetra-hydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, or in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

The application rates of the active compound are from 0.001 to 3.0, preferably from 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

PREPARATION EXAMPLES

Preparation of the Compound I-44

A) Reductive Amination of a Polymer Resin

20 g of 4-(4-formyl-3-methoxyphenoxy)butyryl-aminomethylpolystyrene resin were initially charged in 200 ml of dimethylformamide and 2 ml of acetic acid, 49 ml of methylamine, 10.7 ml of trimethyl orthoformate and 6.2 g of sodium cyanoborhydride were added and the mixture was shaken at 50° C. for 18 hours. After cooling to room temperature, the resin was filtered off, washed with in each case 100 ml of dimethylformamide (2×), methanol (1×), tetrahydrofuran (3×) and dichloromethane (3×) and dried at room temperature.

B) N-Acylation Using a Substituted Phenylalanine Derivative

5 g of the resin prepared in step A were initially charged in 50 ml of dichloromethan/dimethylformamide 1:1, 4.4 g of Fmoc-2-fluorophenylalanine and 5.6 g of benzotriazol-1-yloxy-trispyrrolidinophosphonium hexafluorophosphate (PyBOP) were added and the mixture was shaken at room temperature for 5 min. 1.9 ml of N-methylmorpholine were then added, and the mixture was shaken at room temperature for 18 hours. The resin was filtered off and then washed with in each case 20 ml of dimethylformamide (5×).

C) Removal of the Protective Group X

To remove the Fmoc protective group, the resin was suspended in 50 ml of dimethylformamide/piperidine 1:1 and shaken at room temperature for 1 h. The resin was then filtered off and washed with in each case 20 ml of dimethylformamide (2×), methanol (1×), tetrahydrofuran (3×) and dichloromethane (3×). The resin was dried at room temperature.

D) N-Acylation

250 mg of the resin from step C, 133 mg of 2,4-dichloro-3-(difluoromethyl)benzoic acid and 286 mg of benzotriazol-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (PyBOP) were initially charged in dichloromethane/dimethylformamide 1:1 (2.5 ml). After 5 minutes of shaking, 97 μl of N-methylmorpholine were added, and the mixture was shaken at room temperature for 18 h. The resin was then filtered off and washed with in each case 3 ml of dimethylformamide (2×), methanol (1×), tetrahydrofuran (3×) and dichloromethane (3×). To cleave the product from the solid support, about 2 ml of trifluoroacetic acid/dichloromethane 1:3 were added to the resin. The mixture was shaken for 30 min and then filtered, and the filtrate was concentrated for further use.

*) 2,4-Dichloro-3-(difluoromethyl)benzoic acid was prepared as follows: Reaction of 1,3-dichloro-2-methylbenzene with acetyl chloride and subsequent oxidation to give 1,3-dichloro-2-methylbenzoic acid, conversion of the benzoic acid into the methyl ester, followed by bromination of the methyl group located in position 2, oxidation of the brominated methyl group to give the corresponding aldehyde, fluorination of the resulting product with diethylaminosulfur trifluoride and subsequent hydrolysis of the resulting methyl 2,4-dichloro-2-difluoromethylbenzoate to give 2,4-dichloro-3-(difluoromethyl)benzoic acid.

Yield: 48%

Preparation of the Compound I-32 by Process 4

Step A

13.8 ml of triethylamine were added to 5.29 g of diethyl aminomalonate hydrochloride in 100 ml of dichloromethane. With ice-cooling, trifluoromethylbenzoyl chloride was added to the resulting suspension, which was then shaken at room temperature overnight. The mixture was then extracted with 50 ml of water and the organic phase was separated off and dried over magnesium sulfate.

Step B

0.8 g of 1-(2-fluorophenyl)ethyl methanesulfonate *) and 0.673 g of potassium tert-butoxide were added to 1.27 g of the ester formed in step A in 20 ml of dioxane, and the mixture was incubated at 80° C. with shaking overnight. Water was then added at room temperature, followed by extraction with dichloromethane and subsequent drying over magnesium sulfate.

*) 1-(2-fluorophenyl)ethyl methanesulfonate was prepared from 1-(2-fluorophenyl)ethanol by reaction with methanesulfonic anhydride.

Step C

1 ml of concentrated (about 45% by weight strength) aqueous sodium hydroxide solution was added to 0.8 g of the diester formed in step B in 10 ml of dioxane, and the mixture was incubated at 80° C. with stirring overnight. Water was then added at room temperature. Following addition of hydrochloric acid until a pH of 2 had beep reached, the mixture was extracted with ethyl acetate and the organic phase was separated off and concentrated.

Step D

3.58 g of polymer-bound DCC and 0.315 g of methylamine (40% by volume in water) were added to 0.75 g of the acid formed in step C, the mixture was shaken at room temperature overnight and the resin was filtered off.

The compounds listed in Table I below were prepared by appropriate modification of the process described above. The compounds II required for the synthesis of the compounds were obtained from Fluka and Advanced Chem Tech, the substituted benzoic acids V and the substituted benzoyl chlorides VI were obtained from Aldrich and ABCR and the amines IX were obtained from from Aldrich.

The resulting phenylalanine derivatives of the formula I where R⁴, R⁵, R⁶, R⁸, R¹⁴ and R¹⁵=hydrogen and R⁹=methyl, as shown below,

are listed in Table I together with physical data and the mass signal (M+). The measurements were carried out by by LC-MS (HP-1100, Agilent) using the following conditions:

LC-MS conditions:

-   -   Buffer A (isopropanol, 0.05% trifluoroacetic acid)     -   Buffer B (water, 0.05% trifluoroaceetic acid)     -   Flow rate: 1.2 ml/min     -   Injection volume: 2 μl     -   Fragmentation voltage: 20V, positive ionization mass range         (m/z): 130-700     -   Column: Merck ROD column (50×4.6 mm)

N₂ detection:

-   -   (Method UV-MS-N₂)     -   Injection volume: 5 μl     -   Fragmentation voltage: 20V, positive ionization mass range         (m/z): 130-700         Preparation of Compound II-15 by Process 5         Preparation of the Intermediate         1-(2-fluorophenyl)-1-bromopropane         Step 1

At −20° C., 100 ml of a 1 M solution of ethylmagnesium bromide in THF were added to 10.0 g (0.081 mol) of 2-F-benzaldehyde in 150 ml of THF, the mixture was incubated with stirring for 1.5 h and 100 ml of saturated NH₄Cl solution was added dropwise. The mixture was saturated with NaCl and the organic phase was then separated off, the aqueous phase was extracted with ethyl acetate and the combined organic phases were concentrated.

1H-NMR signals (CDCl₃): 7.6-7.0 (m, 4 H), 5.0 (t, 1 H), 2.0 br.s. 1 H), 1.8 (m, 2 H), 1.0 (t, 3 H)

Yield: 11.2 g as a crude product of a purity of about 70% which was used without further purification for step 2

Step 2

11.2 g of the 1-(2-fluorophenyl)-1-bromopropane obtained in step 1 were dissolved in 150 ml of CH₂Cl₂, 90 ml of a 1 M solution of BBr3 in CH₂Cl₂ were added at 0° C. and the mixture was, after 1 h at 0° C., poured into ice-water. The organic phase was removed and the aqueous phase was then extracted with CH₂Cl₂, and the combined organic phases were concentrated.

1H-NMR signals (CDCl3): 7.4-7.0 (m, 4 H), 5.3 (m, 1 H), 2.3 (m, 1 H), 2.1 (m, 1 H), 1.0 (t, 3 H)

Yield: 14.2 g of the title compound, which was reacted further as a crude product of a purity of about 85%

Preparation of Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycine-N-methylamide (compound II-15)

Step 1

8.61 g of ethyl diphenylmethylideneglycinate, 7.0 g of 1-(1-bromopropyl)-2-fluorobenzene, 13.6 g (0.1 mol) of K2CO3 and 1.06 g (0.003 mol) of tetrabutylammonium bromide in 200 ml of acetonitrile were stirred under reflux for 43 h, cooled and filtered off. After concentration, the filtrate was dissolved in 150 ml of THF and stirred with 150 ml of 10% strength citric acid until the conversion was complete. After removal of the THF, the mixture was extracted with MTBE (methyl tert-butyl ether), the aqueous phase was saturated with K₂CO₃ and the product was extracted 3 times with in each case 100 ml of ethyl acetate. Drying and concentration gave 4.92.4 g of crude product which was used without further purification for the next step.

Step 2

2.4 g of the ethyl 2-(1-methyl-1-(2-(-fluorophenyl))glyinate from step 1 were dissolved in 100 ml of methylene chloride, 3.48 g of NEt3 were added and, at 0° C., 1.27 g (0.01 mol) of 2-trifluoromethyl-4-F-benzoyl chloride were added dropwise. The mixture was stirred at room temperature for 16 h and then diluted with 200 ml of ethyl acetate and washed with in each case 100 ml of 1N HCl and water, and the organic phase was removed under reduced pressure. Chromatographic separation on silica gel (mobile phase cyclohexane/ethyl acetate 8/1) gave 0.7 g of the pure diastereomer A of ethyl Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycinate, 0.22 g of a 1:1 mixture of the two diastereomers A and B of ethyl Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycinate and 0.6 g of the diastereomer B of ethyl Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycinate. Diastereomers A and B were separately characterized by spectroscopy, and all three fractions were then combined for the further conversion in step 3 to 1.55 g of a 1:1 diastereomer mixture.

Signals in the 1H-NMR (CDCl₃) of diastereomer A ethyl (Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycinate): 7.5-7.0 (m, 7 H), 6.1 (br. d 1H), 5.1 (m, 1 H), 4.3 (m, 2 H), 3.5 (m, 1 H9, 2.1-2.0 (m, 2 H), 1.3 (t, 3 H), 1.0 (t, 3 H).

Signals in the 1H-NMR (CDCl₃): of diastereomer B ethyl (Nα-(2-trifluoromethyl-4-fluorobenzoyl)-2-(1-methyl-1-(2-fluorophenyl))glycinate): 7.6-7.0 (m, 7 H), 6.3 (br. d, 1 H), 5.1 (m, 1 H), 4.1 (m, 2 H), 3.3 (m, 1 H), 2.0 (mc 2 H), 1.1 (t, 3 H), 0.8 (t, 3 H).

Step 3

1.5 g of the diastereomer mixture formed in step 2 were dissolved in 100 ml of ethanol. Subsequently, gaseous methylamine was added to the solution until saturation had been reached. After 4 days of stirring at room temperature, the mixture was concentrated and 200 ml of MTBE were added. The resulting solid was filtered off and dried. The resulting product was a 1:1 mixture of the diastereomers of compound II-15.

Yield: 0.261 g

Melting point: 201-202° C.

1H-NMR signals (d6-DMSO): 9.0 (br. d, 1 H), 8.7 (d, 1 H), 8.2 (d, 1 H), 7.8-7.1 (m, 14 H), 6.8 (m, 1 H), 4.9 (m, 1 H), 4.8 (m, 1 H), 3.3 (m, 2 H), 1.9 (m, 1 H), 1.6 (m, 3 H) 2.6 (d, 3 H), 2.4 (d, 3 H), 0.8 (m, 6 H).

The compounds listed in table II below were prepared by modifying the process described above in an appropriate manner. The starting materials required for synthesizing the compounds were obtained from Fluka and Advanced Chem Tech, the substituted benzoic acids V and the substituted benzoyl chlorides VI from Aldrich and ABCR and the amines IX from from Aldrich.

The resulting phenylalanine derivatives of the formula I where R⁹, R¹⁰, R¹⁴ and R¹⁵=hydrogen as shown below

are [lacuna] in table II together with the melting point or physical data (mass signal (M+) and LC-MS mesurements using conditions a or i).

LC-MS conditions a:

-   -   Buffer A (acetonitrile, 0.1% trifluoroacetic acid)     -   Buffer B (water, 0.1% trifluoroacetic acid)     -   Flow rate: 1.8 ml/min     -   Temperature: 80° C.     -   Injection volume: 2 μl     -   Fragmentation voltage: 80V, positive ionization, mass range         (m/z): 100-700     -   Column: Merck ROD column (50×4.6 mm)

LC-MS conditions i:

-   -   Buffer A (isopropanol, 0.05% trifluoroacetic acid)     -   Buffer B (water 0.05% trifluoroacetic acid)     -   Flow rate: 1.5 ml/min     -   Injection volume: 2 μl     -   Temperature: 40° C.     -   Fragmentation voltage: 20V, positive ionization mass range         (m/z): 130-700

Column: Merck ROD column (50×4.6 mm) TABLE I No. R¹ R² R³ R⁷ R¹¹ R¹² R¹³ R¹⁴ Configuration M+ I-1 F H H H F H H H Racemate 319 I-2 F H H H Cl Cl H H Racemate 369 I-3 F H H H CF₃ H H H Racemate 369 I-4 H F H H F H H H Racemate 319 I-5 H F H H Cl Cl H H Racemate 370 I-6 H F H H Br H H H Racemate 380 I-7 H F H H CF₃ H H H Racemate 369 I-8 H Cl H H F H H H Racemate 335 I-9 H Cl H H Cl Cl H H Racemate 386 I-10 H Cl H H Br H H H Racemate 396 I-11 H Cl H H CF₃ H H H Racemate 384 I-12 Cl H H H F H H H Racemate 335 I-13 Cl H H H Cl Cl H H Racemate 386 I-14 Cl H H H Br H H H Racemate 396 I-15 Cl H H H CF₃ H H H Racemate 385 I-16 CH₃ H H H F H H H Racemate 315 I-17 CH₃ H H H Cl Cl H H Racemate 366 I-18 CH₃ H H H Br H H H Racemate 376 I-19 CH₃ H H H CF₃ H H H S 365 I-20 H CH₃ H H F H H H Racemate 315 I-21 H CH₃ H H Cl Cl H H Racemate 366 I-22 H CH₃ H H Br H H H Racemate 376 I-23 H CH₃ H H CF₃ H H H Racemate 365 I-24 H F H H CF₃ F H H S 387 I-25 H F H H CF₃ H H F S 387 I-26 H H H H CF₃ H H H S 351 I-27 H H H H Cl Cl H H Racemate 352 I-28 CH₃ H H H CF₃ H H H Racemate 365 I-29 CH₃ H H H Cl Cl H H Racemate 366 I-30 F H H H CF₃ H H H R 369 I-31 F H H H Cl Cl H H R 370 I-32 F H H CH₃ CF₃ H H H Diastereomer 383 I-33 CH₃ H H H Cl CF₃ H H Racemate 399 I-34 CH₃ H H H CF₃ H F H Racemate 383 I-35 CH₃ H H H CF₃ F H H Racemate 383 I-36 H H F H CF₃ H H H Racemate 369 I-37 H H Cl H CF₃ H H H Racemate 385 I-38 H H F H Cl Cl H H Racemate 370 I-39 H H Cl H Cl Cl H H Racemate 386 I-40 F H H H Cl CF₃ H H S 403 I-41 F H H H Cl H NO₂ H S 380 I-42 F H H H Cl H SO₂CH₃ H S 413 I-43 F H H H Cl CN OCH₃ H S 390 I-44 F H H H Cl CHF₂ Cl H S 420 I-45 F H H H Cl CH₃ NO₂ H S 394 I-46 CH₃ H H H Cl H NO₂ H S 376 I-47 CH₃ H H H Cl H SO₂CH₃ H S 409 I-48 CH₃ H H H Cl CN OCH₃ H S 386 I-49 CH₃ H H H Cl CHF₂ Cl H S 416 I-50 CH₃ H H H Cl CH₃ NO₂ H S 390 I-51 CH₃ H H H CF₃ H F H S 383 I-52 CH₃ H H H Cl CF₃ H H S 399 I-53 CH₃ H H H CF₃ F H H S 383 I-54 F H H H CF₃ H H H S 369 I-55 F H H H Cl Cl H H S 370 I-56 F H H H Cl H Cl H S 370 I-57 F H H H Cl H F H S 353 I-58 CF₃ H H H CF₃ H H H S 419 I-59 CF₃ H H H Cl Cl H H S 419 I-60 CH₃ H H H Cl H Cl H S 365 I-61 CH₃ H H H Cl H F H S 349

TABLE II No. R¹ R² R³ R⁴ R⁵ R⁶ R⁷ R⁸ II-1 F OCH₃ H H H H H CH₃ II-2 H H H CF₃ H H H CH₃ II-3 F H H H H CH₃ H CH₃ II-4 F H H H H H CH₃ CH₃ II-5 CH₂CH₃ H H H H H H CH₃ II-6 F H H H H CH₃ H CH₃ II-7 F H H H H H CH₃ CH₃ II-8 CH₃ H H H H CH₃ H CH₃ II-9 CH₃ H H H H H CH₃ CH₃ II-10 CH₃ H H H H CH₃ H CH₃ II-11 F H H H H (CH₂)₃CH₃ H CH₃ II-12 F H H H H (CH₂)₂CH₃ H CH₃ II-13 CH₃ H H H H (CH₂)₂CH₃ H CH₃ II-14 CH₃ H H H H CH₂CH₃ H CH₃ II-15 F H H H H CH₂CH₃ H CH₃ II-16 F H H H H CH₂CH₃ H CH₃ II-17 CH₃ H H H H CH₂CH₃ H CH₃ II-18 CH₃ H H H CH₃ H H CH₃ II-19 Br H H H H H H CH₃ II-20 Cl Cl H H Cl H H CH₃ II-21 F H H H H (CH₂)₃CH₃ H CH₃ II-22 F H H H H (CH₂)₃CH₃ H CH₃ II-23 F H H H Cl H H CH₃ II-24 F H H H Cl H H CH₃ II-25 H H H H H CH₂CH₃ H CH₃ II-26 OH H H H H H H CH₃ II-27 CF₃ H F H H H H CH₃ II-28 Cl Cl OCH₃ H H H H CH₃ II-29 Cl Cl OCH₃ H H H H CH₃ II-30 F H Cl H H H H CH₃ II-31 F H Cl H H H H CH₃ II-32 OCH₃ H OCH₃ H H H H CH₃ II-33 OCH₃ H H OCH₃ H H H CH₃ II-34 Et H H H H H H CH₃ II-35 OCH₃ H H H H H H CH₃ II-36 OCH₃ H H H H H H CH₃ II-37 NO₂ H H H Cl H H CH₃ II-38 NO₂ H H H Cl H H CH₃ II-39 H CF₃ H CF₃ H H H CH₃ II-40 H CH₃ H CH₃ H H H CH₃ II-41 F F H H H H H CH₃ II-42 H H H H H H H CH₂C(CH)₂ II-43 H H H H H H H CH₂CH(CH₃)₂ II-44 H H H H H H H CH₂CH(CH₃)₂ II-45 H H H H H H H CH₂CH(CH₃)₂ II-46 F H H F Cl H H CH₃ II-47 H CF₃ H F H H H CH₃ II-48 SCF₃ H H H H H H CH₃ II-49 H Br H H H H H CH₃ II-50 H F H F H H H CH₃ II-51 F H H Cl H H H CH₃ II-52 F H H CF₃ H H H CH₃ II-53 Br H H F H H H CH₃ II-54 H OCHF₂ H H H H H CH₃ II-55 F Cl H CF₃ H H H CH₃ II-56 F CH₃ H H F H H CH₃ II-57 F F H F H H H CH₃ II-58 Cl H H CF₃ H H H CH₃ II-59 H SCF₃ H H H H H CH₃ II-60 F H H F H H H CH₃ II-61 NO₂ H H CH₃ H H H CH₃ II-62 F Cl H H H H H CH₃ II-63 Cl H H H Cl H H CH₃ II-64 H OCH₃ H H H H H CH₃ II-65 H OCF₃ H H H H H CH₃ II-66 Cl CF₃ H H H H H CH₃ II-67 NO₂ Cl H H H H H CH₃ II-68 NO₂ H H H H H H CH₃ II-69 H OCH₃ H OCH₃ H H H CH₃ II-70 Cl CH(CH₃)₂ H H H H H CH₃ II-71 CH₃ H H NO₂ H H H CH₃ II-72 F H H H F H H CH₃ II-73 Cl OCH₃ H OCH₃ Cl H H CH₃ II-74 Cl OCH₃ H OCH₃ H H H CH₃ II-75 CN H H H H H H CH₃ II-76 OCHF₂ H H H H H H CH₃ II-77 CH₃ CF₃ H H H H H CH₃ II-78 F CH₃ H H H H H CH₃ II-79 CH₃ H H CH₃ H H H CH₃ II-80 H CH₃ H H H H H CH₃ II-81 F CF₃ H H H H H CH₃ II-82 CH(CH₃)₂ H H H H H H CH₃ II-83 CF₃ H H H H H H CH₃ II-84 CH₃ CH₃ H CH₃ CH₃ H H CH₃ II-85 CH₃ H H H CH₃ H H CH₃ II-86 CH₃ H H F H H H CH₃ II-87 CH₃ Cl H H H H H CH₃ II-88 CH₃ H H CH₃ H H H CH₃ II-89 F CH₃ H H H H H CH₃ II-90 H H H H H H H CH₃ II-91 H H H H H H H CH₃ II-92 H H H F H H H OH II-93 H H H F H H H OCH₃ II-94 H H H H H H H OH II-95 H H H F H H H OCH₃ II-96 F H H F H H H OH II-97 H H H F H H H OCH₃ II-98 H H H F H H H OH II-99 F H H F H H H OH II-100 F H H F H H H CH₃ II-101 H F H H H H H CH₃ II-102 H H H H H H H CH₃ II-103 H H H H H H H CH₃ II-104 CH₃ H H H H H H CH₃ II-105 F H H H H H H CH₃ II-106 H H H H H H H CH₃ II-107 CH₃ H H F H H H CH₃ II-108 F H H H H H H CH₃ II-109 F H H F H H H CH₃ II-110 H H H H H H H CH₃ II-111 CH₃ H H H H H H CH₃ II-112 CH₃ H H H H H H CH₃ II-113 CH₃ H H H H CH₃ H CH₃ LC-MS m.p. No. R⁹ R¹¹ R¹² R¹³ M + H+ cond. [° C.] II-1 H CF₃ H F 208-209 II-2 H CF₃ H F 219-220 II-3 H CF₃ H H 192-193 II-4 H CF₃ H H 231-132 II-5 H CF₃ H F 198-199 II-6 H CF₃ H F 203-204 II-7 H CF₃ H F 213-215 II-8 H CF₃ H H 214-215 II-9 H CF₃ H H 260 II-10 H CF₃ H F 200-201 II-11 H CF₃ H H 204 II-12 H CF₃ H F 206-210 II-13 H CF₃ H F 235-237 II-14 H CF₃ H F 220-222 II-15 H CF₃ H F 201-202 II-16 H CF₃ H H 195-196 II-17 H CF₃ H H 228-230 II-18 H CF₃ H H 224 II-19 H CF₃ H H 430.2 a II-20 H CF₃ H H 454.1 a II-21 H CF₃ H F 198-200 II-22 H CF₃ H F 215-218 II-23 H CF₃ H H 205-207 II-24 H CF₃ H F 215-216 II-25 H CF₃ H H 205-206 II-26 H CF₃ H F 215-216 II-27 H CF₃ H F 210-211 II-28 H CF₃ H F 253-254 II-29 H CF₃ H H 236-237 II-30 H CF₃ H F 209-210 II-31 H CF₃ H H 220-221 II-32 H CF₃ H H 229-230 II-33 H CF₃ H F 226-227 II-34 H CF₃ H F 188-190 II-35 H CF₃ H H 216-217 II-36 H CF₃ H F 196-197 II-37 H CF₃ H F 203-204 II-38 H CF₃ H H 212-214 II-39 H CF₃ H H 487.1 a II-40 H CF₃ H H 379.1 a II-41 H CF₃ H H 387.1 a II-42 H CF₃ H F 393.1 a II-43 H CF₃ H F 395.0 a II-44 H CF₃ H H 375.1 a II-45 H CF₃ H H 377.1 a II-46 H CF₃ H H 421.0 a II-47 H CF₃ H H 437.1 a II-48 H CF₃ H H 451.1 a II-49 H CF₃ H H 429.0 a II-50 H CF₃ H H 387.1 a II-51 H CF₃ H H 403.1 a II-52 H CF₃ H H 437.1 a II-53 H CF₃ H H 449.0 a II-54 H CF₃ H H 417.1 a II-55 H CF₃ H H 471.0 a II-56 H CF₃ H H 401.1 a II-57 H CF₃ H H 405.1 a II-58 H CF₃ H H 453.0 a II-59 H CF₃ H H 451.0 a II-60 H CF₃ H H 387.1 a II-61 H CF₃ H H 410.1 a II-62 H CF₃ H H 403.1 a II-63 H CF₃ H H 419.0 a II-64 H CF₃ H H 381.1 a II-65 H CF₃ H H 435.1 a II-66 H CF₃ H H 453.1 a II-67 H CF₃ H H 430.0 a II-68 H CF₃ H H 396.1 a II-69 H CF₃ H H 411.1 a II-70 H CF₃ H H 427.1 a II-71 H CF₃ H H 410.1 a II-72 H CF₃ H H 200-201 II-73 H CF₃ H H 229-230 II-74 H CF₃ H H 220-221 II-75 H CF₃ H H 232-233 II-76 H CF₃ H H 187-188 II-77 H CF₃ H F 451.4 i II-78 H CF₃ H F 401.4 i II-79 H CF₃ H F 397.4 i II-80 H CF₃ H F 383.4 i II-81 H CF₃ H F 455.4 i II-82 H CF₃ H F 411.4 i II-83 H CF₃ H F 455.4 i II-84 H CF₃ H F 425.4 i II-85 H CF₃ H F 397.4 i II-86 H CF₃ H F 401.4 i II-87 H CF₃ H H 223-224 II-88 H CF₃ H H 379.4 i II-89 H CF₃ H H 437.4 i II-90 H CF₃ H H 365.1 a II-91 H CF₃ H F 369.1 a II-92 H CF₃ H H 320.1 a II-93 H CF₃ H H 320.1 a II-94 CH₃ CF₃ H F 338.1 a II-95 H CF₃ H F 338.1 a II-96 H CF₃ H F 352.0 a II-97 H CF₃ H H 320.0 a II-98 H CF₃ H F 338.0 a II-99 H CF₃ H F 358.1 a II-100 H CF₃ H F 389.0 a II-101 H F H H 305.1 a II-102 H F CF₃ H 369.1 a II-103 H F F H 319.1 a II-104 H Cl Cl H 352.1 a II-105 H Cl Cl H 356.1 a II-106 H Cl Cl H 352.1 a II-107 H Cl CF₃ H 398.81 a II-108 H Cl H Cl 370.0 a II-109 H Cl Cl F 353.0 a II-110 H Cl H Cl 352.1 a II-111 H SO₂CH₃ H H 375.1 a II-112 H SO₂CHF₂ H H 379.0 a II-113 H Cl CF₃ H 413.84 a Use Examples for Herbicidal Action

The herbicidal activity of the phenylalanine derivatives of the formula I was demonstrated by greenhouse experiments:

The cultivation containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, directly after sowing, the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.095, 0.5 or 1.91 kg of a.s. (active substance).

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over from 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the following species: Scientific name Common name Abutilon theophrasti velvetleaf Setaria italica foxtail millet Sinapis alba white mustard Chenopodium album common lambsquarters Setaria faberia giant foxtail Galium aperine catchweed Polygonum persicaria ladysthumb

Compound I-19 provides very good control of Abutilon theophrasti and Setaria italica when applied by the post-emergence method at application rates of 0.5.kg of a.s./ha.

Compound I-24 provides very good control of Abutilon theophrasti and Sinapis alba when applied by the post-emergence method at application rates of 0.5 kg of a.s./ha.

Compound I-25 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 0.5 kg of a.s./ha.

Compound I-32 provides very good control of Setaria italica and Sinapis alba when applied by the post emergence method at application rates of 0.095 kg of a.s./ha.

Compound I-49 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 1.91 kg of a.s./ha.

Compound I-49 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 3.0 kg of a.s./ha.

Compound I-51 provides very good control of Abutilon theophrasti and Chenopodium album when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Compound I-53 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 0.5 kg of a.s./ha.

Compound II-91 provides very good control of Abutilon theophrasti and Sinapis alba when applied by the post-emergence method at application rates of 2.0 kg of a.s./ha.

Compound II-87 provides very good control of Setaria faberia and Chenopodium album when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Compound II-94 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 3.0 kg of a.s./ha.

Compound II-111 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Compound II-112 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Compound II-15 provides very good control of Abutilon theophrasti, Setaria italica and Sinapis alba when applied by the post-emergence method at application rates of 0.5 kg of a.s./ha.

Compound II-10 provides very good control of Chenopodium album, Galium aperine and Polygonum persicaria when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Compound II-7 provides very good control of Abutilon theophrasti and Chenopodium album when applied by the post-emergence method at application rates of 1.0 kg of a.s./ha.

Use Examples for Growth-Regulating Action

The growth-regulating action of the phenylalanine derivatives of the formula I was demonstrated by greenhouse experiments:

The cultivation containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, directly after sowing, the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of from 3 to 15 cm, depending on the plant habit, and then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.5 kg of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over from 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

At the end of the experiment, the observed growth-regulating action was recorded by measuring the height of growth. The measured values obtained in this manner were compared to the height of growth of untreated plants.

Compound II-92, when applied post-emergence at a rate of 500 g/ha, had a significant impact on the longitudinal growth of Zea mays L. 14 days after application (see Tab. III) TABLE III Compound Height in cm Plant II-92 31-33 Zea mays L. Untreated 40-42 Zea mays L. 

1-16. (canceled)
 17. A phenylalanine derivative of the formula I

in which R¹, R², R⁴, R⁵, R¹³ and R¹⁵ independently of one another are hydrogen, halogen, hydroxyl, mercapto, nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C6-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₃ -C₆-haloalkynylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₃ -C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy, C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy, C₃-C₆-alkynylthio-C₁-C₄ -alkoxy, C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶; R³ is hydrogen, halogen, mercapto, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkinyl, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₆-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl or CO—R¹⁶; R⁶ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl; R⁷ is hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl or C₂-C₆-haloalkynyl; R⁸ is methyl, ethyl, C₁-C₆-alkoxy or hydroxyl; R⁹ is hydrogen or C₁-C₆-alkyl; R¹⁰ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl or C₁-C₆-haloalkoxylcarbonyl; R¹¹ is halogen, mercapto, nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, C₂-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy, C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy, C₃-C₆-alkynylthio-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy, C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶; R¹² and R¹⁴ independently of one another are hydrogen, halogen, hydroxyl, mercapto, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₃-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₆-haloalkylthio, C₂-C₆-haloalkenylthio, C₃-C₆-haloalkynylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₃-C₆-haloalkynylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl, C₃-C₆-haloalkynylsulfonyl, formyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₆-alkenyloxy-C₁-C₄-alkyl, C₃-C₄-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl, C₃-C₆-alkenylthio-C₁-C₄-alkyl, C₃-C₄-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, C₁-C₆-alkyloxycarbonyl -C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₃-C₆-alkenyloxy-C₁-C₄-alkoxy, C₃-C₄-alkynyloxy-C₁-C₄-alkoxy, C₁-C₆-alkylthio-C₁-C₄-alkoxy, C₃-C₆-alkenylthio-C₁-C₄-alkoxy, C₃-C₆-alkynylthio-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyl-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkoxy, C₁-C₆-alkyloxycarbonyl-C₁-C₄-alkoxy or CO—R¹⁶; and R¹⁶ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino; or R⁷ together with R¹⁰ forms a C₃-C₄-alkylene or -alkenylene chain, where the C₃-C₄-alkylene or -alkenylene chain may carry 1-3 substituents from the group consisting of halogen, nitro or cyano and/or one carbon atom of the C₃-C₄-alkylene chain may be replaced by a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen and/or by a carbonyl group; or an argiculturally useful salt thereof.
 18. A phenylalanine derivative or salt thereof as claimed in claim 17, in which R¹ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₁-C₆-haloalkylsulfonyl or C₃-C₆-haloalkenylsulfonyl; R² is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy or C₃-C₆-haloalkynyloxy; R³ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁴ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy; R⁵ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₃-C₆-haloalkenyloxy; and R₆ is hydrogen or C₁-C₆-alkyl; R⁷ is hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₁-C₆-haloalkyl; R⁸ is methyl, ethyl, hydroxyl or methoxy; R⁹ is hydrogen or methyl; R¹⁰ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl or C₁-C₄-haloalkoxycarbonyl; R¹¹ is halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃₋C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl or CO—R¹⁶; R¹³ is hydrogen, halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-haloalkenylsulfonyl or CO—R¹⁶; R¹² and R¹⁴ independently of one another are hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-alkenylthio, C₃-C₆-alkynylthio, C₁-C₆-alkylsulfinyl, C₃-C₆-alkenylsulfinyl, C₃-C₆-alkynylsulfinyl, C₁-C₆-alkylsulfonyl, C₃-C₆-alkenylsulfonyl, C₃-C₆-alkynylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₃-C₆-haloalkenylthio, C₁-C₆-haloalkylsulfinyl, C₃-C₆-haloalkenylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆ -haloalkenylsulfonyl or CO—R¹⁶; R¹⁵ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R¹⁶ is hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino.
 19. A phenylalanine derivative or salt thereof as claimed in claim 17 in which R¹ is hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl; R² is hydrogen, halogen, cyano, C₁-C₆-haloalkyl or C₁-C₆-alkyl; R³ is hydrogen, C₁-C₆-alkyl or halogen; R⁴ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁵ is hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁶ is hydrogen or C₁-C₆-alkyl; R⁷ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl; R⁸ is methyl, hydroxyl or methoxy; R⁹ is hydrogen or methyl; R¹⁰ is hydrogen; and R¹¹ is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl or C₁-C₆-alkylsulfinyl; R¹², R¹³ and R¹⁴ independently of one another are hydrogen, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or C₁-C₆-haloalkylthio; and R¹⁵ is hydrogen.
 20. A phenylalanine derivative or salt thereof as claimed in claim 17 in which R¹, R², R³, R⁵ in each case independently of one another are hydrogen, fluorine, chlorine, methyl or ethyl; R⁴, R⁶, R¹⁰, R¹⁴and R¹⁵ are hydrogen; R⁷ is hydrogen, methyl or ethyl; R⁸ is methoxy methyl or hydroxyl; R⁹ is hydrogen; is methyl if R⁸ is hydroxyl; R¹¹ is fluorine, chlorine, halomethyl such as fluoromethyl, difluoromethyl, trifluoromethyl, halomethoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, halothioalkyl, such as fluorothiomethyl, difluorothiomethyl, trifluorothiomethyl, methylsulfinyl or methylsulfonyl; R¹² is hydrogen, cyano, methyl, fluorine, chlorine, halomethyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, halomethoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, halothioalkyl, such as fluorothiomethyl, difluorothiomethyl, trifluorothiomethyl; R¹³ is hydrogen, fluorine, chlorine.
 21. A process for preparing a phenylalanine derivative of claim 17 comprising (A) linking a phenylalanine derivative of the formula II

which is protected at the amino function by a protective group X to a support resin; (B) removing the protective group X by addition of a base, (C) acylating the resulting compounds at the nitrogen and (D) cleaving the compounds acylated at the nitrogen from the solid support by addition of an acid, followed by addition of a condensing agent with an amine IX R⁸—NH—R⁹   (IX) to produce a phenyalanine derivative of claim
 17. 22. A process for preparing a phenylalanine derivative of claim 17 in which R⁹ is hydrogen, comprising (A) reacting a polymer resin X Pol-CHO   (X) with an amine XI H²NR⁸   (XI) in the presence of a reducing agent to obtain an aminated resin; (B) reacting the aminated resin XII Pol-CH₂—NHR⁸   (XII) obtained in step A with a phenylalanine derivative of the formula II;

(C) removing the protective group X by addition of a base; (D) and acylating the resulting compounds XIII

to give the compound, XIV

which is subsequently, by addition of an acid, cleaved from the solid support, thereby preducing a compound of claim
 17. 23. A process for preparing phenylalanine derivatives of as claimed in claim 17 comprising (A) reacting a phenylalanine derivative of the formula II

which is protected at the amino function by a protective group X, with an amine IX HNR⁸R⁹   (IX) in an inert aprotic dipolar organic solvent to give the compounds XV

(B) removing the protective group X, and (C) acylating the compounds obtained in step B to give a compound of formula I.
 24. A process for preparing phenylalanine derivative of claim 17 in which R⁹ is hydrogen, comprising (A) reacting an aminomalonic acid ester derivative XVII

in which R′ is a low-molecular-weight organic radical with a benzyl derivative XVIII

to give a diester XIX

(B) decarboxylating and hydrolyzing the diester XIX, followed by reaction with an amine IX HNR⁸R⁹   (IX) in an inert aprotic dipolar organic solvent using a condensing agent, to provide a compound of formula I.
 25. A process for preparing a phenylalanine derivative of claim 17 comprising (A) reacting the benzyl derivative XVIII

with an alkylating agent XXI

to give the compound XXII

(B) acylating the resulting compound XXII at the nitrogen and (C) reacting the nitrogen-acylated compounds by addition of a condensing agent with an amine IX R⁸—NH—R⁹   (IX) to produce a phenylalanine derivative of claim
 17. 26. An argicultural composition comprising a phenylalanine derivative of claim 17 or an agriculturally useful salt thereof and at least one customary auxiliary.
 27. An argicultural composition suitable for controlling undesirable vegetation which composition comprises a phenylalanine derivative of claim 17 or an agriculturally useful salt thereof and a solid liquid carrier.
 28. A method for controlling undesirable vegetation comprising contacting at least one of the vegetation or the vetetation's habitat or seed with an effective amount of a phenylalanine derivative of claim 17 or an argiculturally useful salt thereof.
 29. A composition for regulating plant growth comprising a growth-regulating effective amount of at least one phenylalanine derivative of claim 17 or an agriculturally useful salt thereof and at least one inert solid or liquid carrier.
 30. The composition of claim 29, further comprising at least one surfactant.
 31. A process for preparing compositions for regulating plant growth, said process comprising mixing a growth-regulating effective amount of at least one phenylalanine derivative of claim 17 or an aguiculturally useful salt thereof with at least one liquid or solid carrier.
 32. The process of claim 31, further comprising mixing at least one surfactant into the composition.
 33. A method for regulating plant growth, comprising contacting a plant with a growth-regulating effective amount of at least one phenylalanine derivative of claim 17 or an agriculturally useful salt thereof. 